Kinetic studies on the influence of micellar aggregates upon the hydrolysis and transnitrosation reactions of N-methyl-N-nitrosotoluene-p-sulphonamide

Abstract

The basic hydrolysis of N-methyl-N-nitrosotoluene-p-sulphonamide and its transnitrosation reaction with secondary amines (sarcosine and dimethylamine) have been studied in the presence of cationic, anionic, and non-ionic micelles. The results show that the electric charge of the nucleophile is essential for the understanding of the micellar effects, which can be quantitatively rationalized on the basis of the pseudophase kinetic model. Thus the reaction with negatively charged nucleophiles is inhibited by both anionic and non-ionic surfactants, whereas cationic micelles increase the reaction rate, which passes through a maximum. The reaction between the substrate and a neutral nucleophile is, however, inhibited by all three classes of surfactant.