Decomposition of N-chloro-α-amino acids in alkaline medium

Abstract

The decomposition of the N-Cl and N-Br derivatives of L-glycine and L-sarcosine in alkaline medium shows a first-order dependence, with respect to the N-halo-α-amino acid and to the concentration of hydroxide ions. From the leaving group effect and the primary deuterium kinetic isotope effect, and in the framework of the principle of non-perfect synchronization, the conclusion can be drawn that the decomposition of the N-halo-α-amino acids in alkaline medium can be satisfactorily described through an (A_xhD_HD_N) mechanism with a carbanion and reactant-like transition state.