E(2)-Elimination in the Decomposition of N-Bromoamino Acid Anions

The kinetics of oxidation of eight structurally different amino acids by hypobromite ion (BrO(-)) in the presence of hydroxide ion has been studied. The reactions proceed through the rapid formation of N-bromoamino acid anion which then decomposes in the rate-limiting step. The decomposition of N-bromoamino acid anions is found to proceed through an unimolecular and a base-catalyzed reaction. The large negative values of DeltaS() and the products formed suggest that the hydroxide ion-catalyzed reactions proceed through an E(2) mechanism. N-Bromoamino acid anion gives an absorption spectrum with lambda(max) at approximately 290 nm.