Solvent effects on the free energies of the reactants and transition states in the Menschutkin reaction of trimethylamine with alkyl halides

Abstract

In the reaction of trimethylamine with p-nitrobenzyl chloride, the variation of the free energy of the transition state with solvent is generally larger than the corresponding variation in the sum of the free energies of the reactants, but in the reaction of trimethylamine with methyl iodide the accelerating effect of solvent water is entirely due to a large increase in the free energy of the reactants.