The kinetics and mechanism of the mercurous ion-promoted hydrolysis of S-thio esters
Abstract
The kinetics of the mercurous ion-promoted hydrolysis of three p-substituted S-ethyl thiobenzoates have been studied. It has been established that the mercurous ion is a powerful soft acid with a strength lying between those of the mercuric and silver ions. The sequence of ester reactivity is p-MeO > p-H p-NO2. The substituent effects, the values of the activation parameters, and the effects of pH changes all suggest that for the p-NO2 derivative the hydrolysis mechanism is AAc2, but that for the other two esters the mechanism is AAc1.