Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin
The cyclization of ethyl 2-(aminosulfonyl)benzoate (ASB) to give saccharin was investigated in aqueous solutions at pH between 5.2 and 9.5 and in the temperature range of 296.2-334.2 K. The initial concentration of the reactant was varied between 1.45 × 10-5 and 3.86 × 10-4 M. Ultraviolet spectrosco...
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todo:paper_00456535_v49_n3_p353_DiLoreto2023-10-03T14:52:00Z Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin Di Loreto, H.E. Czarnowski, J. Dos Santos Afonso, M. Cyclization Degradation products of sulfonylurea herbicides Ethyl 2-(aminosulfonyl)benzoate Kinetics Saccharin Catalysis Hydrolysis pH effects Rate constants Reaction kinetics Solutions Spectroscopy Pseudo-first-order kinetics Organic compounds benzoic acid derivative ethyl 2 (aminosulfonyl)benzoate herbicide saccharin unclassified drug kinetics aqueous solution article cyclization hydrolysis molecular dynamics temperature dependence ultraviolet spectroscopy water contamination Benzoic Acids Catalysis Cyclization Hydrogen-Ion Concentration Hydrolysis Kinetics Saccharin Spectrophotometry, Ultraviolet Sulfonamides Temperature Water Pollutants, Chemical Kobus The cyclization of ethyl 2-(aminosulfonyl)benzoate (ASB) to give saccharin was investigated in aqueous solutions at pH between 5.2 and 9.5 and in the temperature range of 296.2-334.2 K. The initial concentration of the reactant was varied between 1.45 × 10-5 and 3.86 × 10-4 M. Ultraviolet spectroscopy was used to obtain the kinetic data. The reaction is acid catalyzed and follows pseudo-first-order kinetics. The experimental rate constant, kobs, increases with temperature and pH. Its dependence on the temperature and pH is well described by: kobs = k1[OH-] = [(2.52 ± 0.9) × 1016 exp(-20.2 ± 1 kcalmol-1/RT) s-1][OH-] A mechanism is proposed and the half-life of ethyl ASB is calculated. © 2002 Elsevier Science Ltd. All rights reserved. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00456535_v49_n3_p353_DiLoreto |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Cyclization Degradation products of sulfonylurea herbicides Ethyl 2-(aminosulfonyl)benzoate Kinetics Saccharin Catalysis Hydrolysis pH effects Rate constants Reaction kinetics Solutions Spectroscopy Pseudo-first-order kinetics Organic compounds benzoic acid derivative ethyl 2 (aminosulfonyl)benzoate herbicide saccharin unclassified drug kinetics aqueous solution article cyclization hydrolysis molecular dynamics temperature dependence ultraviolet spectroscopy water contamination Benzoic Acids Catalysis Cyclization Hydrogen-Ion Concentration Hydrolysis Kinetics Saccharin Spectrophotometry, Ultraviolet Sulfonamides Temperature Water Pollutants, Chemical Kobus |
| spellingShingle |
Cyclization Degradation products of sulfonylurea herbicides Ethyl 2-(aminosulfonyl)benzoate Kinetics Saccharin Catalysis Hydrolysis pH effects Rate constants Reaction kinetics Solutions Spectroscopy Pseudo-first-order kinetics Organic compounds benzoic acid derivative ethyl 2 (aminosulfonyl)benzoate herbicide saccharin unclassified drug kinetics aqueous solution article cyclization hydrolysis molecular dynamics temperature dependence ultraviolet spectroscopy water contamination Benzoic Acids Catalysis Cyclization Hydrogen-Ion Concentration Hydrolysis Kinetics Saccharin Spectrophotometry, Ultraviolet Sulfonamides Temperature Water Pollutants, Chemical Kobus Di Loreto, H.E. Czarnowski, J. Dos Santos Afonso, M. Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin |
| topic_facet |
Cyclization Degradation products of sulfonylurea herbicides Ethyl 2-(aminosulfonyl)benzoate Kinetics Saccharin Catalysis Hydrolysis pH effects Rate constants Reaction kinetics Solutions Spectroscopy Pseudo-first-order kinetics Organic compounds benzoic acid derivative ethyl 2 (aminosulfonyl)benzoate herbicide saccharin unclassified drug kinetics aqueous solution article cyclization hydrolysis molecular dynamics temperature dependence ultraviolet spectroscopy water contamination Benzoic Acids Catalysis Cyclization Hydrogen-Ion Concentration Hydrolysis Kinetics Saccharin Spectrophotometry, Ultraviolet Sulfonamides Temperature Water Pollutants, Chemical Kobus |
| description |
The cyclization of ethyl 2-(aminosulfonyl)benzoate (ASB) to give saccharin was investigated in aqueous solutions at pH between 5.2 and 9.5 and in the temperature range of 296.2-334.2 K. The initial concentration of the reactant was varied between 1.45 × 10-5 and 3.86 × 10-4 M. Ultraviolet spectroscopy was used to obtain the kinetic data. The reaction is acid catalyzed and follows pseudo-first-order kinetics. The experimental rate constant, kobs, increases with temperature and pH. Its dependence on the temperature and pH is well described by: kobs = k1[OH-] = [(2.52 ± 0.9) × 1016 exp(-20.2 ± 1 kcalmol-1/RT) s-1][OH-] A mechanism is proposed and the half-life of ethyl ASB is calculated. © 2002 Elsevier Science Ltd. All rights reserved. |
| format |
JOUR |
| author |
Di Loreto, H.E. Czarnowski, J. Dos Santos Afonso, M. |
| author_facet |
Di Loreto, H.E. Czarnowski, J. Dos Santos Afonso, M. |
| author_sort |
Di Loreto, H.E. |
| title |
Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin |
| title_short |
Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin |
| title_full |
Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin |
| title_fullStr |
Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin |
| title_full_unstemmed |
Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin |
| title_sort |
kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin |
| url |
http://hdl.handle.net/20.500.12110/paper_00456535_v49_n3_p353_DiLoreto |
| work_keys_str_mv |
AT diloretohe kineticsofhydrolysisandcyclizationofethyl2aminosulfonylbenzoatetosaccharin AT czarnowskij kineticsofhydrolysisandcyclizationofethyl2aminosulfonylbenzoatetosaccharin AT dossantosafonsom kineticsofhydrolysisandcyclizationofethyl2aminosulfonylbenzoatetosaccharin |
| _version_ |
1807319164982919168 |