The results of kinetic studies on the reactions of 2-phenyl-l-propyl arenesulfonates with anilines and benzylamines in methanol at $55.0^{circ}C$ are reported. The transition state variation with the substituents in the nucleophile (X) and leaving group (Z) is in accord with that expected from a negative ${sigma}_{XZ}$ value. A stronger nucleophile and nucleofuge lead to a greater extent of bond-making and -breaking. Somewhat greater magnitude of ${sigma}_{XZ}$ compared to the nearly constant value for the similar processes at a primary carbon atom has been interpreted to result from a partial contribution of the concurrent frontal displacement path.