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Oxidation of 2‐Phenylethylamine with N ‐Bromosuccinimide in Acid and Alkaline Media: A Kinetic and Mechanistic Study
Author(s) -
Mohana Kikkeri N.,
Ramdas Bhandarkar Paanemangalore M.
Publication year - 2007
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200700173
Subject(s) - chemistry , n bromosuccinimide , hydrochloric acid , ionic strength , oxidizing agent , reaction rate , stoichiometry , inorganic chemistry , reagent , nuclear chemistry , organic chemistry , catalysis , halogenation , aqueous solution
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 = k[NBS][PEA][H + ] in hydrochloric acid medium and ‐d [NBS]/dt = k[NBS][PEA] x [OH − ] 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.