Spectroscopic Evidence for a New Type of Bonding between a Thioether Radical Cation and a Phenyl Group

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 p...

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Published inOrganic letters Vol. 15; no. 19; pp. 4932 - 4935
Main Authors Monney, Nicolas P.-A, Bally, Thomas, Bhagavathy, Ganga S, Glass, Richard S
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 04.10.2013
Subjects
Cations - chemistry
Electrons
Molecular Structure
Oxidation-Reduction
Sulfides - chemistry
Sulfur - chemistry
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol402126f