Kinetics and Mechanism of Oxidation of Phenylalanine and Serine by Chloramine-T

Department of Chemistry, University of Allahabad, Allahabad-211002, India

Manuscript received 28 December 1974 ; revised 24 November 1975 ; accepted 31 March 1976

Oxidation of phenylalanine and serine by chloramine-T in alkaline media has been investiga­ted. The proposed mechanism involves two schemes. The first is followed by the major fraction of the reaction and proceeds through the interaction between a-amino acid molecule and p-toluene­sulphochloramide in a slow and rate determining step resulting in the formation of an intermediate which subsequently attacks another molecule of p-toluenesulphochloramide in a fast step yield­ing the products. The second involves a minor fraction of the reaction in which hypochlorite ion replaces p-toluenesulphochloramide in the above steps. The schemes interpret the observed data satisfactorily. Various thermodynamic parameters have been computed and nitriles identified as the end products.