Reactivity of a-Amino Acids in the N-Acylation with Benzoic Acid Esters in Aqueous Dioxane

摘要

The effect of the nitro group as a substituent in the phenoxide part of phenyl benzoate on the rate of N-acylation of glycine, L-proline,and L-valine in the water (40 wt %)-dioxane solvent was studied. The activation parameters of glycine reactions with the esters were measured. The existence of compensation effect and the linear relation of the logarithms of the acylation constants to the Hammett constants were revealed. The energy of the LUMO of esters can serve as the descriptors of the easters reactivity.