doi: 10.1021/ja1083046.
Epub 2010 Nov 4.
The redox chemistry of sulfenic acids
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- PMID: 21049943
- DOI: 10.1021/ja1083046
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The redox chemistry of sulfenic acids
J Am Chem Soc.
.
Abstract
A persistent triptycenyl sulfenic acid is used as a model for cysteine-derived and other biologically relevant sulfenic acids in experiments which define their redox chemistry. EPR spectroscopy reveals that sulfinyl radicals are persistent and unreactive toward O(2), allowing the O-H bonding dissociation enthalpy (BDE) of the sulfenic acid to be readily determined by equilibration with TEMPO as 71.9 kcal/mol. The E° (RSO•/RSO(-)) and pK(a) of this sulfenic acid are also reported.
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