Substituent Effects on the Micelle-Catalysed and Uncatalysed Basic Hydrolysis of a Series of Substituted N-Methyl-p-toluanilides

Abstract

The rate of hydrolysis of a series of substituted N-methyl-p-toluanilides has been measured in water and in the presence of cationic micelles [cetyltrimethylammonium bromide (ctab)]. A Hammett correlation of the rates of hydrolysis gave a curved Hammett plot for the reaction in water (k_2,W) but a linear plot for the rate of reaction at optimal concentrations of ctab (k_2,max) and for derived rate constants within the micelle (k_2,m) These results are discussed in terms of the mechanism of reaction, and for two compounds a micelle-induced change of mechanism is indicated.