The redox chemistry of sulfenic acids |
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| Authors: | McGrath Alaina J Garrett Graham E Valgimigli Luca Pratt Derek A |
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| Institution: | Department of Chemistry, Queen's University, 90 Bader Lane, Kingston, Ontario, Canada K7L 3N6. |
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| 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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