Carbonion (ElcB) mechanism of ester hydrolysis. I. Hydrolysis of malonate esters

B Holmquist, TC Bruice

Index: Holmquist,B.; Bruice,T.C. Journal of the American Chemical Society, 1969 , vol. 91, p. 2993 - 3002

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Citation Number: 45

Abstract

Abstract: The pH-log rate profiles for the hydrolysis of ethyl o-nitrophenyl malonate (I), ethyl o- nitrophenyl methylmalonate (111), ethyl p-nitrophenyl methylmalonate (IV), and ethyl o- nitrophenyl dimethylmalonate (V) have been determined in water at 30”) ionic strength= 1.0. Ester V hydrolyzes via the expected spontaneous general-base water-catalyzed and hydroxide-catalyzed mechanisms. Esters I, 111, and IV, which contain a-protons, have ...