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IJC-A Vol.48A(08) [August 2009] >

Title: Oxidative cleavage of gabapentin with N-bromosuccinimide in acid medium: A kinetic and mechanistic study
Authors: Bhandarkar, P M Ramdas
Mohana, K N
Keywords: Kinetics
Reaction mechanisms
Issue Date: Aug-2009
Publisher: CSIR
IPC CodeInt. Cl.9 C07B33/00
Abstract: The kinetics of oxidative degradation of gabapentin with N-bromosuccinimide in HClO4­ medium has been studied at 308 K. The experimental rate law obtained is d[NBS] /dt = [NBS][GBP]x[H+]y, where x and y are less than unity. The reaction was subjected to changes in concentration of succinimide, the reduction product of NBS, concentration of the added neutral salt, dielectric permittivity and ionic strength of the medium. Solvent isotope effect has been studied using D2O. The stoichiometry of the reaction has been found to be 1:1, and oxidation products have been identified and characterized by FTIR and 1H NMR spectral studies. Activation parameters for the overall reactions have been computed from Arrhenius plot. (CH2CO)2N+HBr has been postulated as the reactive oxidizing species. The oxidation reaction fails to induce polymerization of the added acrylonitrile. The proposed mechanism and the derived rate law are consistent with the observed kinetic data.
Page(s): 1107-1112
ISSN: 0975-0975 (Online); 0376-4710 (Print)
Source:IJC-A Vol.48A(08) [August 2009]

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