Steric Effects on the Oxidation Potential of 1-aryl Thioglycosides

Authors

MEHMET A. OTURAN
MAURICE MEDEBIELLE
SHIRISH A. PATIL
ROBERT S. KLEIN

Abstract

The electrochemical oxidation of several 1-arylthioglycosides has been studied by cyclic voltammetry in acetonitrile. We found that the oxidation potential of the \alpha anomer always occurs at a less positive oxidation potential than of the \beta 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.

DOI

-

Keywords

Thioglycosides, cyclic voltammetry, oxidation potentials, steric effects.

First Page

317

Last Page

322

Recommended Citation

OTURAN, MEHMET A.; MEDEBIELLE, MAURICE; PATIL, SHIRISH A.; and KLEIN, ROBERT S. (2002) "Steric Effects on the Oxidation Potential of 1-aryl Thioglycosides," Turkish Journal of Chemistry: Vol. 26: No. 3, Article 3. Available at: https://journals.tubitak.gov.tr/chem/vol26/iss3/3