Oxidation of Pentoses by Sodium-N-bromo-P-toluene sulphonamide: A Kinetic and Mechanistic Study

Iyengar, T. A. and Mahadevappa, D. S. (1992) Oxidation of Pentoses by Sodium-N-bromo-P-toluene sulphonamide: A Kinetic and Mechanistic Study. Journal of Carbohydrate Chemistry, 11 (1). pp. 37-58.

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Official URL: https://doi.org/10.1080/07328309208016140

Abstract

Kinetics of oxidation of D-xylose, D-ribose, D-lyxose and L-arabinose by bromamine-T (sodium N-bromo-p-toluene sulphonamide, BAT) was studied in alkaline medium at 30-degrees-C. The rate was zero-order in BAT], but exhibited fractional order kinetics with respect to sugar] and HO-]. The rates levelled off at higher sugar] and HO-]. Stoichiometry experiments have shown that the sugar was oxidised to the respective aldonic acid. Variation of ionic strength of medium and addition of the reaction products, p-toluenesulphonamide and Cl- ions have no effect on the rate. The rate increased with decrease in dielectric constant of the medium. Solvent isotope studies using D2O have shown that k(s) (D2O)/ k(s) (H2O) = 1.36. The reaction has been studied at different temperatures and the overall activation parameters have been calculated. Activation parameters for the rate limiting step were determined from Michaelis-Menton type plots. A mechanism in which formation of the enediol anion of the sugar is the rate limiting step is proposed.

Item Type: Article
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Users 23 not found.
Date Deposited: 13 May 2021 05:21
Last Modified: 07 Jan 2023 06:00
URI: http://eprints.uni-mysore.ac.in/id/eprint/16468

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