Oxidation of erythrose series sugars by sodium N-chlorobenzenesulphonamide in alkaline medium: A kinetic study

M. P. Raghavendra, K. S. Rangappa, D. S. Mahadevappa, D. Channe Gowda

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8 Scopus citations

Abstract

The kinetics of oxidation of D-glucose, D-mannose, D-fructose, D-arabinose, and D-ribose, with sodium N-chlorobenzenesulphonamide (chloramine-B or CAB) in alkaline medium have been studied at 35°C and the rate law, rate = κ′ [CAB] [Sugar] [OH-]2 is observed. The rate of reaction is influenced by a change in ionic strength of the medium, and the dielectric effect is negative. The solvent isotope studies in D2O show that the rate is almost doubled in heavy water. HPLC and GLC-MS analyses of the products indicated that the erythrose-series sugars are oxidized to a mixture of aldonic acids consisting of arabinonic, ribonic, erythronic, and glyceric acids in varying proportions. Based on these data, a mechanism involving the aldoenolic aniońs of pentoses and keto-enolic anions of hexoses is suggested.

Original languageEnglish (US)
Pages (from-to)783-792
Number of pages10
JournalIndian Journal of Chemistry - Section B Organic and Medicinal Chemistry
Volume37
Issue number8
StatePublished - Dec 1 1998

All Science Journal Classification (ASJC) codes

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

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