Kinetics and mechanism of oxidation of D-mannosamine by sodium N-chloro-p-toluenesulphonamide in alkaline medium
- Rangappa, K.S.
- Mahadevappa, D.S.
- Raghavendra, M.P.
DOIAbstract
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 e...
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