Kinetics and mechanism of phosphate-catalyzed hydrolysis of benzoate esters: comparison with nucleophilic catalysis by imidazole and o-iodosobenzoate

…, MF Ruasse, WA Rodrigues

Index: El Seoud, Omar A.; Ruasse, Marie-Francoise; Rodrigues, Wagner A. Journal of the Chemical Society. Perkin Transactions 2, 2002 , # 6 p. 1053 - 1058

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Citation Number: 14

Abstract

Phosphate-catalyzed hydrolysis of 2, 4-dinitrophenyl 4-X-benzoate, and 3-or 4-Y-phenyl 3, 5- dinitrobenzoates, where X and Y are substituents, has been studied spectrophotometrically. The following conclusions are based on catalytic rate constants, solvent kinetic isotope effect, detection of a mixed anhydride by FTIR, and application of the Hammett equation:(i) the catalytically active species is HPO42−,(ii) the mechanism of catalysis is nucleophilic, ...