Kinetics and mechanism of oxidation of some α-amino acids by benzyltrimethylammonium chiorobromate

Abstract

The oxidation of nine α-amino acids by benzyltlimethylammonium chlorobromate (BTMACB) in aqueous acetic acid leads to the formation of the corresponding carbonyl compounds. The reaction is first order each with respect to the amino acid and BTMACB. The reaction does not induce the polymerization of acrylonitrile. There is no effect of added benzyltrimethylammonium chloride or bromide ion on the reaction rate. The oxidation of perdeuterioglycine shows the absence of a kinetic isotope effect. The effect of solvent composition indicates that the reaction rate increases with an increase in the polarity of the

solvent. Chlorobromate ion has been postulated as the reactive oxidizing species. The reaction is susceptible to both polar and steric effects of the substituents. A suitable mechanism has been proposed.