• DOI:10.1080/07328309208016140
• Corpus ID: 85347187

Oxidation of pentoses by sodium-N-bromo-P-toluene sulphonamide : a kinetic and mechanistic study

@article{Iyengar1992OxidationOP,
  title={Oxidation of pentoses by sodium-N-bromo-P-toluene sulphonamide : a kinetic and mechanistic study},
  author={Tirumala A. Iyengar and Dandinasivara S. Mahadevappa},
  journal={Journal of Carbohydrate Chemistry},
  year={1992},
  volume={11},
  pages={37-58}
}

• T. A. Iyengar, D. Mahadevappa
• Published 1992
• Chemistry
• Journal of Carbohydrate Chemistry

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 °C. The rate was zero-order in [BAT]0, but exhibited fractional order kinetics with respect to [sugar]0, and [HO−]0. The rates levelled off at higher [sugar]0, and [HO−]0. Stoichioaetry 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 Dg0 have shown that ks(DgO)/ ks.(HgO) = 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 r...