Application of a Hammett–Taft relation to kinetics of strecker degradation of α-amino-acids with phenalene-1,2,3-trione hydrate

Abstract

The reaction rates of α-amino-acids with phenalene-1,2,3-trione hydrate have been studied as a function of pH of the reaction medium, pK₂ of the amino-group, temperature, and structure of the amino-compounds. From the pH–rate profile, it was possible to postulate the rate-determining step, i.e., attack of amino-acid as a free base on a carbonyl group of the trione. A quantitative estimate of the influence of the steric and polar parameters on the rates was obtained from a Hammett–Taft free energy relationship.