Oxidation of 2-Phenylethylamine with N-Bromosuccinimide in acid and alkaline media: A kinetic and mechanistic study

Mohana, K. N. and Ramdas Bhandarkar, Paanemangalore M. (2007) Oxidation of 2-Phenylethylamine with N-Bromosuccinimide in acid and alkaline media: A kinetic and mechanistic study. Journal of the Chinese Chemical Society, 54 (5). pp. 1223-1232. ISSN 2192-6549

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Official URL: https://doi.org/10.1002/jccs.200700173

Abstract

A kinetic study of oxidation of 2-phenylethylamine (PEA), a bioactive compound, with potent oxidant, N-bromosuccinimide (NBS) has been carried out in HCl and NaOH media at 313 K. The experimental rate laws obtained are: -d NBS /dt = kNBSPEAH+ in hydrochloric acid medium and -d NBS/dt = kNBSPEAxOH−y in alkaline medium where x and y are less than unity. Accelerating effect of Cl−, and retardation of the added succinimide on the reaction rate have been observed in acid medium. Variation of ionic strength of the medium shows negligible effect on rate of reaction in both media. Decrease in dielectric permittivity of the medium decreased the rate in both media. The stoichiometry of the reaction was found to be 1:1 in acid medium and 1:2 in the case of alkaline medium. The oxidation products of PEA were identified as the corresponding aldehyde and nitrile in acid and alkaline medium, respectively. The reactions were studied at different temperatures and the activation parameters have been evaluated. The reaction constants involved in the proposed mechanisms were computed. The reaction was found to be faster in alkaline medium in comparison with the acid medium, which is attributed to the involvement of different oxidizing species. The proposed mechanisms and the derived rate laws are consistent with the observed experimental results.

Item Type: Article
Uncontrolled Keywords: Oxidation kinetics, N-Bromosuccinimide, Acid and alkaline media, 2-Phenylethylamine
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: C Swapna Library Assistant
Date Deposited: 07 Sep 2019 09:12
Last Modified: 07 Sep 2019 09:12
URI: http://eprints.uni-mysore.ac.in/id/eprint/7762

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