Effect of acyl substituents on the reaction mechanism for aminolyses of 4-nitrophenyl X-substituted benzoates

IH Um, JS Min, JA Ahn, HJ Hahn

Index: Um, Ik-Hwan; Min, Ji-Sook; Ahn, Jung-Ae; Hahn, Hyun-Joo Journal of Organic Chemistry, 2000 , vol. 65, # 18 p. 5659 - 5663

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Citation Number: 100

Abstract

Second-order rate constants (k N) have been measured spectrophotometrically for the reaction of 4-nitrophenyl X-substituted benzoates with a series of alicyclic secondary amines in H2O containing 20 mol% dimethyl sulfoxide at 25.0° C. The magnitude of the k N values increases with increasing the basicity of amines and with increasing the electron- withdrawing ability of the acyl substituent X. The Hammett plots obtained are not linear but ...