Abstract

We herein report on the group electrophilicity of molecular fragments present in the title compounds to describe leaving group abilities in reactions of aryl benzoates toward CN . It is found that the presence of electron-withdrawing substituents in the permanent group enhances its electrophilicity, thereby contributing to the stabilization of the tetrahedral intermediate involved in the stepwise pathway. On the other hand electron-releasing substituents attached to the permanent group enhance the nucleofugality of the leaving groups in these systems. Substituent effects are used to rationalize the activation/deactivation patterns induced by electron-withdrawing and electron-releasing groups at the aromatic rings.