Oxidative cleavage of gabapentin with N-bromosuccinimide in acid medium: a kinetic and mechanistic study

Bhandarkar, Ramdas P. M. and Mohana, K. N. (2009) Oxidative cleavage of gabapentin with N-bromosuccinimide in acid medium: a kinetic and mechanistic study. INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY, 48 (8). pp. 1107-1112. ISSN 0975-0975

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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 H-1 NMR spectral studies. Activation parameters for the overall reactions have been computed from Arrhenius plot. (CH2CO)(2)N+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.

Item Type: Article
Uncontrolled Keywords: Kinetics; Reaction mechanisms; Oxidations; Gabapentin
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Shrirekha N
Date Deposited: 20 Aug 2019 07:00
Last Modified: 20 Aug 2019 07:00
URI: http://eprints.uni-mysore.ac.in/id/eprint/6806

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