Kinetics and mechanism of the oxidation of uronic acdis by sodium N-chlorobenzenesulphonamide in alkaline medium

Article abstract of DOI:10.1080/07328309708006535

The kinetics of oxidation of D-glucuronic acid and D-galacturonic acid (UA) by sodium N-chlorobenzenesulphonamide or chloramine-B (CAB) in alkaline medium at 35°C has been investigated and the rate law, rate = k [CAB][UA][HO^-] was observed. The product, benzenesulphonamide had no influence. Increase of ionic strength increased the rate and when the dielectric constant of the medium was decreased, the rate was decreased. The rate increased in D₂O medium and the inverse solvent isotope effect k (D₂O)/k (H₂O) was 2.00. Proton inventory was studied for the reactions in H₂O-D₂O mixtures. Activation parameters have been determined from the Arrhenius plots. The mechanism assumes the formation of an enediol anion followed by its oxidation by the positive halogen in a rate limiting step.

Full text of DOI:10.1080/07328309708006535

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Kinetics and Mechanism of the
Oxidation of Uronic Acids by Sodium N-
Chlorobenzenesulphonamide in Alkaline
Medium
a
a
a
K. S. Rangappa , M. P. Raghavendra & D. S. Mahadevappa
a
Department of Studies in Chemistry , University of Mysore ,
Manasagangotri, Mysore, 570 006, India
Published online: 19 Aug 2006.
To cite this article: K. S. Rangappa , M. P. Raghavendra & D. S. Mahadevappa (1997) Kinetics and
Mechanism of the Oxidation of Uronic Acids by Sodium N-Chlorobenzenesulphonamide in Alkaline
Medium, Journal of Carbohydrate Chemistry, 16:3, 359-371, DOI: 10.1080/07328309708006535
To link to this article: http://dx.doi.org/10.1080/07328309708006535
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