Abstract

The kinetics and the mechanism of oxidation of creatine (AA) by N-Bromosuccinimide (NBS) in an acidic aqueous medium were examined under isolation conditions. Iodometric method was used to follow the unconsumed NBS at different time intervals. Mercuric(II) acetate was used as a scavenger to capture any Br- formed during the reaction and hence to avoid autocatalytic oxidation by bromine. Findings from stoichiometry measurements revealed that the reaction between AA and NBS was a 2:1 molar ratio. The kinetic study showed that the reaction was first order with respect to both AA and NBS. Increasing [H+] had a negative effect on the rate of reaction. The effect that varying the solvent composition has on the rate of reaction was investigated, and it was found that the reaction rate decreased as the dielectric constant of the solvent increased. The temperature dependence was determined under fixed experimental conditions, from which thermodynamic parameters were calculated. From the proposed mechanism, a rate law was established that was in strong agreement with experimental kinetics.

Highlights

  • N-Bromosuccinimide (NBS) is one of the oxidants that is widely used in oxidising organic compounds.[1,2,3,4,5] It is used to oxidise many inorganic complexes, as well as biochemical compounds.[] NBS is a source of positive halogen, and this reagent has been exploited as an oxidant for a variety of substrates in neutral, acidic and alkaline mediums

  • Stoichiometric measurements were taken by carrying different sets of reaction mixtures containing different amounts of NBS and creatine at a constant concentration of [H+] and a constant ionic strength

  • This study has reported the kinetics and mechanism of oxidation of creatine by NBS in acidic aqueous solution

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Summary

Introduction

N-Bromosuccinimide (NBS) is one of the oxidants that is widely used in oxidising organic compounds.[1,2,3,4,5] It is used to oxidise many inorganic complexes, as well as biochemical compounds.[] NBS is a source of positive halogen, and this reagent has been exploited as an oxidant for a variety of substrates in neutral, acidic and alkaline mediums. NBS has been used as a reagent in the determination of some chemical compounds. Haiyan et al determined meloxicam by oxidation with NBS using the flow-injection chemiluminescence technique, and the same technique was used to determine urea.[13,14] Fluorometric assays carried out by Lee et al for commercial NBS indicated that NBS reagents could be assayed rapidly using a convenient method.[15] Xu et al used NBS for the oxidation of indoles to produce different pharmaceutically valuable nitrogen compounds.[16]

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