The redox chemistry of sulfenic acids

AJ McGrath, GE Garrett, L Valgimigli…

Index: McGrath, Alaina J.; Garrett, Graham E.; Valgimigli, Luca; Pratt, Derek A. Journal of the American Chemical Society, 2010 , vol. 132, # 47 p. 16759 - 16761

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Citation Number: 34

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 O2, 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 p K a of this ...