Intramolecular reorganization 1. Deprotonation of toluene with the CH2CN− anion: an analysis in the framework of a gas-phase model

Abstract

A mechanism is proposed of intramolecular reorganization leading to equalization of the energies of reactants and products in a nonequilibrium proton transfer reaction. The model proposed allows one to extend a conventional quantum chemical treatment to gas-phase proton transfer. Taking the reaction of toluene deprotonation with the CH2CN− anion (a conjugate base of acetonitrile) as an example, it was shown that the activation energy and its components can be determined from direct ab initio calculations. The effect of disbalance of structural changes relative to the “equilibrium” proton transfer is considered.