Faculté des sciences

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.

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

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... Plus

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    Summary
    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.