Kinetics and mechanism of oxidation of erythro-series pentoses and hexoses by N-Chloro-p-toluenesulfonamide (cas 144-86-5)

Add time:09/28/2019    Source:infona.pl

The kinetics and mechanism of oxidation of d-glucose, d-mannose, d-fructose, d-arabinose, and d-ribose with chloramine-T in alkaline medium were studied. The rate law, rate=k [Chloramine-T] [Sugar] [HO - ] 2 , was observed. The rate of the reaction was influenced by a change in ionic strength of the medium, and the dielectric effect was found to be negative. The latter enabled the computation of d A B , the size of the activated complex. The reaction rate was almost doubled in deuterium oxide. Activation energies were calculated from the Arrhenius plots. HPLC and GLC-MS analyses of the products indicated that the sugars were oxidized to a mixture of aldonic acids, consisting of arabinonic, ribonic, erythronic, and glyceric acids. Based on these data, a plausible mechanism involving the aldo-enolic anions of pentoses and keto-enolic anions of hexoses is suggested.

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