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Pure Appl. Chem., 2010, Vol. 82, No. 3, pp. 555-563

Published online 2010-02-18

Anodic oxidation of m-terphenyl thio-, seleno- and telluroethers: Lowered oxidation potentials due to chalcogen···π interaction

Malika Ammam1, Uzma I. Zakai2, George S. Wilson3 and Richard S. Glass4*

1 Department of Metallurgy and Materials Engineering, Catholic University of Leuven, Leuven, Belgium
2 Department of Chemistry, University of Wisconsin, Madison, WI 53706, USA
3 Department of Chemistry, The University of Kansas, Lawrence, KS 66045, USA
4 Department of Chemistry, The University of Arizona, Tucson, AZ 85721, USA

Abstract: The electrochemistry of m-terphenylthio-, seleno-, and telluroethers was studied using cyclic voltammetry in acetonitrile. All of the compounds studied showed irreversible oxidations. The first oxidation potentials for the thio- and selenoethers are less positive than expected. This facilitation in oxidation is ascribed to through-space S···π and Se···π inter-action, respectively, on removal of an electron. No evidence for a comparable effect was found for the phenyltelluro-ethers studied.