Kinetics of N‐bromination of 2‐oxazolidinone

Abstract

The kinetics of N-bromination of 2-oxazolidinone by transfer of Br from sodium hypobromite, N-bromosuccinimide (NBS), or N-bromoacetamide (NBA) were determined spectrophotometrically, at pH between 4.6 and 12.45 (depending on the brominating agent). The reaction with hypobromite was of first order with respect to both the hypobromite and the substrate. The bromination of oxazolidinone with NBS (or NBA) has been found to be a reversible process of order one with respect to both NBA (or NBA) and oxazolidinone in the forward direction, and order one with respect to SI (or ACAM) and the resulting N-bromo-oxazolidinone in the other. The pH dependence of the reaction rate was in keeping with a mechanism in which all the brominating agents (HOBr, BrO − , NBS and NBA) react predominantly with the anion of the substrate. Bimolecular bromination rate constants increased in the order BrO − < NBA <

Kinetic study of the formation reaction of N-chloro-2-oxazolidinone

“…On the other hand, in the literature, a kinetic study of N ‐bromination of OXA with N ‐bromosuccinimide was found . Comparing the results obtained in this work with literature data, it can be confirmed that the reactions of N‐bromination of nitrogenous organic compounds are faster than the corresponding reactions of N ‐chlorination.…”

“…The values for the activation energy obtained in this work were compared with others obtained under similar conditions, which were found in the literature. It was found that they are of the same order of magnitude as those obtained for the reaction of this nitrogenous compound with its analogous N ‐brominating agent (NBS), and with those obtained for the N ‐chlorination reaction of the nitrogenous compound with these chlorinating agents (HOCl, t BuOCl, and NCS) …”

“…In the literature, kinetic studies on the reaction of these amines with other reagents such as NO + , Cl + , and Br + have been found. In these studies, the kinetic results are very similar to those found in the present work.…”