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

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

doi:10.1021/ol402126f

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

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

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

33 Scopus citations

Abstract

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 Sπ bonding that reveals itself in the photoelectron spectrum and by an electronic transition involving the orbitals participating in the Sπ bond.

Original language	English (US)
Pages (from-to)	4932-4935
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	19
DOIs	https://doi.org/10.1021/ol402126f
State	Published - Oct 4 2013

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol402126f

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title = "Spectroscopic evidence for a new type of bonding between a thioether radical cation and a phenyl group",

abstract = "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 Sπ bonding that reveals itself in the photoelectron spectrum and by an electronic transition involving the orbitals participating in the Sπ bond.",

author = "Monney, \{Nicolas P.A.\} and Thomas Bally and Bhagavathy, \{Ganga S.\} and Glass, \{Richard S.\}",

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T1 - Spectroscopic evidence for a new type of bonding between a thioether radical cation and a phenyl group

AU - Monney, Nicolas P.A.

AU - Bally, Thomas

AU - Bhagavathy, Ganga S.

AU - Glass, Richard S.

PY - 2013/10/4

Y1 - 2013/10/4

N2 - 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 Sπ bonding that reveals itself in the photoelectron spectrum and by an electronic transition involving the orbitals participating in the Sπ bond.

AB - 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 Sπ bonding that reveals itself in the photoelectron spectrum and by an electronic transition involving the orbitals participating in the Sπ bond.

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U2 - 10.1021/ol402126f

DO - 10.1021/ol402126f

M3 - Article

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EP - 4935

JO - Organic Letters

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ER -

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

Abstract

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