AN AB-INITIO SCRF CONTINUUM STUDY OF THE LEWIS-ACID COMPLEXATION OF ESTERS

A theoretical quantum mechanical study of the Lewis acid complexation of esters in solution is presented. Calculations have been performed f or the complexation of BH3 and BF3 to methyl acetate. The ab initio Ve rsion of the polarizable continuum model has been used to describe the solvent effect. Changes in the conformational preference of methyl ac etate induced upon complexation have been examined. The relevance of t he solvent effect is determined from the comparison of the interaction energies for the complexes in gas phase and in aqueous solution. Resu lts indicate that both the Lewis acid and the solvent play an active r ole in modulating the reactivity at the carbonyl center, and that a ca reful choice of these factors is essential in determining the reactivi ty of esters derivatives.