KINETICS AND MECHANISM OF THE OXIDATION OF α-AMINO ACIDS BY N-BROMOACETAMIDE

Article abstract of DOI:10.1016/S0040-4020(01)91446-2

The kinetics of the oxidation of eight α-amino acids by N-bromoacetamide have been studied in aqueous perchloric acid solution.The main products of the oxidation are the corresponding carbonyl compounds.The reaction is of first order with respect to the oxidant and the amino acid.The rate of oxidation decreases linearly with an increase in hydrogen ion concentration.The rate is decreased by the addition of acetamide.The oxidation of deuteriated glycine indicated the absence of a primary kinetic isotope effect.The reaction rate has been determined at different temperatures and activation parameters have been caculated.Hypobromous acid has been postulated as the reactive oxidizing species.A rate-determining reaction of the neutral amino acid and hypobromous acid to give an N-bromo derivative has been proposed.The slow step is followed by a fast decomposition of the N-bromo derivative to yield the ultimate product.