"Kinetic and Thermodynamic Studies of Amino Acid Esters"

Abstract

Taft has shown that the rates of alkaline hydrolysis of aliphatic carboxylic acid esters are governed by a combination of electronic, or inductive effects and steric effects. This conclusion was based on kinetic data for the hydrolysis of a wide variety of acyl – substituted ethyl acetates. The naturally occurring α–amino acids, RCH(NH2)COOH, where R represents a wide variety of substituents, provide another series of aliphatic carboxylic acids which display a range of structural type. It therefore seemed of considerable interest to measure the rate of basic hydrolysis of a wide variety of methyl and ethyl α–amino acid esters, in order to determine the extent to which the hydrolytic rate constants were governed by inductive or steric effects.