KINETIC-STUDIES ON THE AMINOLYSIS OF 2-PHENYL-1-PROPYL ARENESULFONATES IN METHANOL

The results of kinetic studies on the reactions of 2-phenyl-1-propyl a renesulfonates with anilines and benzylamines in methanol at 55.0-degr ees-C are reported. The transition state variation with the substituen ts in the nucleophile (X) and leaving group (Z) is in accord with that expected from a negative rho(XZ) value : A stronger nucleophile and n ucleofuge lead to a greater extent of bond-making and -breaking. Somew hat greater magnitude of rho(XZ) compared to the nearly constant value for the similar processes at a primary carbon atom has been interpret ed to result from a partial contribution of the concurrent frontal dis placement path.