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

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

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	783-792
Number of pages	10
Journal	Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry
Volume	37
Issue number	8
State	Published - 1998

All Science Journal Classification (ASJC) codes

General Pharmacology, Toxicology and Pharmaceutics
Organic Chemistry

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

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 anio{\'n}s of pentoses and keto-enolic anions of hexoses is suggested.",

author = "Raghavendra, {M. P.} and Rangappa, {K. S.} and Mahadevappa, {D. S.} and {Channe Gowda}, D.",

year = "1998",

language = "English (US)",

volume = "37",

pages = "783--792",

journal = "Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry",

issn = "0376-4699",

publisher = "Scientific Publishers of India",

number = "8",

}

TY - JOUR

T1 - Oxidation of erythrose series sugars by sodium N-chlorobenzenesulphonamide in alkaline medium

T2 - A kinetic study

AU - Raghavendra, M. P.

AU - Rangappa, K. S.

AU - Mahadevappa, D. S.

AU - Channe Gowda, D.

PY - 1998

Y1 - 1998

N2 - 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.

AB - 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.

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UR - http://www.scopus.com/inward/citedby.url?scp=0542380513&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0542380513

SN - 0376-4699

VL - 37

SP - 783

EP - 792

JO - Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

JF - Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

IS - 8

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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