Journal of the American Chemical Society

Carboxylic acid participation in amide hydrolysis. Evidence that separation of a nonbonded complex can be rate determining

R Kluger, J Chin

Index: Kluger, Ronald; Chin, Jik Journal of the American Chemical Society, 1982 , vol. 104, # 10 p. 2891 - 2897

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Citation Number: 38

Abstract

Abstract: Maleamic acids derived from aliphatic amines of a wide range of basicity (compounds 1-8) undergo hydrolysis in solutions of acidity between IO4 M and 1 M hydrogen ion concentration by a mechanism involving participation of the carboxyl group at the adjacent amide. Kinetic analysis of the reaction (50" C) reveals that the identity of the rate-determining step (or steps) is a function of both the basicity of the leaving group and ...