Steric Effects on the Oxidation Potential of 1-aryl Thioglycosides

The electrochemical oxidation of several 1-arylthioglycosides has been studied by cyclic voltammetry in acetonitrile. We found that the oxidation potential of the a anomer always occurs at a less positive oxidation potential than of the b anomer. The difference in the oxidation potential depends on the substituent attached on the C-3 of the sugar moiety and is greatly influenced by the stability of the radical cation obtained after the first electron transfer.

Steric Effects on the Oxidation Potential of 1-aryl Thioglycosides

The electrochemical oxidation of several 1-arylthioglycosides has been studied by cyclic voltammetry in acetonitrile. We found that the oxidation potential of the a anomer always occurs at a less positive oxidation potential than of the b anomer. The difference in the oxidation potential depends on the substituent attached on the C-3 of the sugar moiety and is greatly influenced by the stability of the radical cation obtained after the first electron transfer.