Kinetic and theoretical studies on the mechanism of intramolecular catalysis in phenyl ester hydrolysis

ANDRÉS,G. O.; PIERINI, A. B.; DE ROSSI, R. H.

JOURNAL OF ORGANIC CHEMISTRY

American Chemical Society

Año: 2006 vol. 71 p. 7650 - 7650

0022-3263

he kinetic study of the hydrolysis reaction of Z-substituted phenyl hydrogen maleates (Z = H, m-CH3, p-CH3, m-Cl, p-Cl and m-CN) was carried out in aqueous solution, and the results were complemented with theoretical studies. Under some experimental conditions, two kinetic processes were observed. One of them was ascribed to maleic anhydride formation and the other to the anhydride hydrolysis. The Bronsted-type plot for the leaving-group dependence was linear with slope blg = -1. The experimental results are consistent with a mechanism th