Nucleophilic substitution at sulphur. Reaction of p-nitrophenyl triphenylmethanesulphenate with n-butylamine and benzamidine

Abstract

The reaction of n-butylamine with p-nitrophenyl triphenylmethanesulphenate is of the second order in nucleophile, but the reaction of benzamidine with the same substrate in the same solvent is of the first order in nucleophile. The same pattern is found when n-butylamine and benzamidine react with carboxylic esters and aromatic derivatives. It is suggested that this pattern has a common origin and that the first-order behaviour of benzamidine can be explained without resorting to bifunctional catalysis.