Kinetics and mechanism of oxidation of erythro-series pentoses and hexoses by N-chloro-p-toluenesulfonamide

Kanchugarakoppal S. Rangappa, Manikanahally P. Raghavendra, Dandinasivara S. Mahadevappa, D. Channe Gowda

Research output: Contribution to journalArticle

29 Scopus citations

Abstract

The kinetics and mechanism of oxidation of D-glucose, D-mannose, D- fructose, D-arabinose, and D-ribose with chloramine-T in alkaline medium were studied. The rate law, rate = k [Chloramine-T] [Sugar] [HO-]2, was observed. The rate of the reaction was influenced by a change in ionic strength of the medium, and the dielectric effect was found to be negative. The latter enabled the computation of d(AB), the size of the activated complex. The reaction rate was almost doubled in deuterium oxide. Activation energies were calculated from the Arrhenius plots. HPLC and GLC-MS analyses of the products indicated that the sugars were oxidized to a mixture of aldonic acids, consisting of arabinonic, ribonic, erythronic, and glyceric acids. Based on these data, a plausible mechanism involving the aldo-enolic anions of pentoses and keto-enolic anions of hexoses is suggested.

Original languageEnglish (US)
Pages (from-to)57-67
Number of pages11
JournalCarbohydrate Research
Volume306
Issue number1-2
DOIs
StatePublished - Jan 1 1998

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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