The redox chemistry of sulfenic acids.

Alaina J McGrath, Graham E Garrett, Luca Valgimigli, Derek A Pratt

Department of Chemistry, Queen's University, 90 Bader Lane, Kingston, Ontario, Canada K7L 3N6.

Journal of the American Chemical Society 2010 Dec 1

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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.

Citation

Alaina J McGrath, Graham E Garrett, Luca Valgimigli, Derek A Pratt. The redox chemistry of sulfenic acids. Journal of the American Chemical Society. 2010 Dec 1;132(47):16759-61