Spectroscopic evidence for a new type of bonding between a thioether radical cation and a phenyl group

Monney, Nicolas P.-A.; Bally, Thomas; Bhagavathy, Ganga S.; Glass, Richard S.

doi:10.1021/ol402126f

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Spectroscopic evidence for a new type of bonding between a thioether radical cation and a phenyl group

Monney, Nicolas P.-A. Department of Chemistry, University of Fribourg, Switzerland,
Bally, Thomas Department of Chemistry, University of Fribourg, Switzerland,
Bhagavathy, Ganga S. Department of Chemistry and Biochemistry, The University of Arizona, Tucson, United States
Glass, Richard S. Department of Chemistry and Biochemistry, The University of Arizona, Tucson, United States

04.10.2013

Published in:

Organic Letters. - 2013, vol. 15, no. 19, p. 4932–4935

English The oxidation potential of thioethers constrained to be near aromatic rings is lowered, due to an antibonding interaction between the p-type sulfur lone pair with the neighboring phenyl π-system which on removal of an electron becomes a new kind of 3-electron S∴π bonding that reveals itself in the photoelectron spectrum and by an electronic transition involving the orbitals participating in the S∴π bond.

Faculty

Faculté des sciences et de médecine

Department

Département de Chimie

Language