Aminolysis of Y-substituted phenyl X-substituted benzoates with piperidine: Effect of nonleaving group substituent

Abstract

The title reaction has been suggested to proceed through a zwitterionic tetrahedral intermediate with a change in the rate determining step on the basis of the curved Brønsted-type plots obtained. The curvature center of the curved Brønsted-type plots is at pKa = 6.4 regardless of the electronic nature of the substituent X in the benzoyl moiety. © 2006 American Chemical Society.