Micellar catalysis of the basic hydrolysis of anilides. III. α-Substituted N-methyl-N-p-nitrophenylacetamides

Abstract

The basic hydrolysis of a number of α-substituted N-methyl-N-p- nitrophenylacetamides has been studied both in the presence and absence of micelles of cetyltrimethylammonium bromide (ctab). Unlike the related p-nitrophenyl esters of a-substituted acetic acids, no evidence for the operation of the E1cb mechanism in the basic hydrolysis has been detected. Reasons for the differences between the amides and esters are discussed. Substituent effects on the hydrolysis of the amides have been studied both by single-parameter and dual-parameter analysis.