Anodic oxidation of <em>m</em>-terphenyl thio-, seleno- and telluroethers: Lowered oxidation potentials due to chalcogen&middot;&middot;&middot;&pi; interaction

Ammam, Malika; Zakai, Uzma I.; Wilson, George S.; Glass, Richard S.

doi:10.1351/PAC-CON-09-08-10

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

http://dx.doi.org/10.1351/PAC-CON-09-08-10

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.