Substituent effects on the basic methanolysis of a series of substituted N-Methyl-p-toluanilides

Abstract

The rate of basic methanolysis of a series of substituted N-methyl-p- toluanilides (1) has been measured at 373 K. A Hammett plot of these results resulted in a straight line (p 3.1, r 0.998) indicative of reaction by solvent-assisted bond breaking (mechanism B) throughout the series. The relevance of these results to previous results for the basic hydrolysis of N-methyl-p-toluanilides (I) and basic methanolysis of N-methylbenzanilides (2) is discussed.