Rangappa, K. S. and Mahadevappa, D. S. and Raghavendra, M. P. (1997) Kinetics and mechanism of oxidation of D-mannosamine by sodium N-chloro-p-toluenesulphonamide in alkaline medium. Indian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry, 36 (10). pp. 890-896.
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The kinetics of oxidation of D-mannosamine (S) to the aldonic acids by sodium N-chloro-p-toluenesulphonamide or chloramine-T (CAT) in the presence of alkali at 40 degrees C follows the rate law dCAT]/dt=kCAT] S] HO-](x), where x<1. Increase of ionic strength increases the rate. The rate decreases when the dielectric constant of medium decreases. The inverse solvent isotope effect k(D2O)/k(H2O)was found to be 1.62. The mechanism assumes stepwise, the formation of sugar alkoxy anion, followed by a rate limiting complexation with oxidant resulting in the formation of the respective pentose through decarboxylation and deamination. The latter is oxidised to arabonic, ribonic, erythronic and glyceric acids. A mechanism involving the reaction of enolanion of sugar with the oxidant in the rate limiting step is proposed.
| Item Type: | Article |
|---|---|
| Subjects: | C Chemical Science > Chemistry |
| Divisions: | Department of > Chemistry |
| Depositing User: | Users 23 not found. |
| Date Deposited: | 02 Jun 2021 06:37 |
| Last Modified: | 05 Jul 2022 07:37 |
| URI: | http://eprints.uni-mysore.ac.in/id/eprint/16599 |
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