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Université de Fribourg

Proline as a charge stabilizing amino acid in peptide radical cations

Monney, Nicolas P.-A. ; Bally, Thomas ; Giese, Bernd

In: Journal of Physical Organic Chemistry, 2015, vol. 28, no. 5, p. 347–353

Long distance electron transfer in proteins requires relay stations that can be transitorily oxidized or reduced. Although individual prolines cannot assume this function, because of their high ionization energy, it has been shown that polyprolines have the ability to transfer charges. In order to determine the role of the proline in the hole distribution and transport within a PheProPhe...

Université de Fribourg

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...