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Abstract:

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.

Registro:

Documento: Artículo
Título:Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin
Autor:Di Loreto, H.E.; Czarnowski, J.; Dos Santos Afonso, M.
Filiación:Laboratorio de Compuestos OrgánicosLADECOM, Facultad de Ciencias Exactas, Universidad Nacional de la Plata, 1900 La Plata, Argentina
Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas, Sucursal 4, Casilla de Correo 16, 1900 La Plata, Argentina
Facultad de Ciencias Exactas y Naturales, INQUIMAE-Departamento de Quimica Inorganica, Analitica y Química Física Univ. de Buenos Aires Ciudad Univ., Pabellón II, 3er. Piso, C1428EHA Buenos Aires, Argentina
Palabras clave: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
Año:2002
Volumen:49
Número:3
Página de inicio:353
Página de fin:361
DOI: http://dx.doi.org/10.1016/S0045-6535(02)00279-5
Título revista:Chemosphere
Título revista abreviado:Chemosphere
ISSN:00456535
CAS:Benzoic Acids; ethyl 2-(aminosulfonyl)benzoate; Saccharin, 81-07-2; Sulfonamides; Water Pollutants, Chemical
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00456535_v49_n3_p353_DiLoreto

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Citas:

---------- APA ----------
Di Loreto, H.E., Czarnowski, J. & Dos Santos Afonso, M. (2002) . Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin. Chemosphere, 49(3), 353-361.
http://dx.doi.org/10.1016/S0045-6535(02)00279-5
---------- CHICAGO ----------
Di Loreto, H.E., Czarnowski, J., Dos Santos Afonso, M. "Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin" . Chemosphere 49, no. 3 (2002) : 353-361.
http://dx.doi.org/10.1016/S0045-6535(02)00279-5
---------- MLA ----------
Di Loreto, H.E., Czarnowski, J., Dos Santos Afonso, M. "Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin" . Chemosphere, vol. 49, no. 3, 2002, pp. 353-361.
http://dx.doi.org/10.1016/S0045-6535(02)00279-5
---------- VANCOUVER ----------
Di Loreto, H.E., Czarnowski, J., Dos Santos Afonso, M. Kinetics of hydrolysis and cyclization of ethyl 2-(aminosulfonyl)benzoate to saccharin. Chemosphere. 2002;49(3):353-361.
http://dx.doi.org/10.1016/S0045-6535(02)00279-5