Electron spin resonance studies. Part XLVI. Oxidation of thiols and disulphides in aqueous solution: formation of RS˙, RSO˙, RSO2˙, RSSR–, and carbon radicals

Bruce C. Gilbert; Hugh A. H. Laue; Richard O. C. Norman; Roger C. Sealy

doi:10.1039/P29750000892

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Electron spin resonance studies. Part XLVI. Oxidation of thiols and disulphides in aqueous solution: formation of RS˙, RSO˙, RSO₂˙, RSSR^–̣, and carbon radicals

Bruce C. Gilbert, Hugh A. H. Laue, Richard O. C. Norman and Roger C. Sealy

Abstract

Radicals which mediate in the oxidation of thiols with the Ti^III–H₂O₂ couple and Ce^IV and of disulphides with the former reagent, in aqueous solution at room temperature, have been studied by e.s.r. spectroscopy. The e.s.r. evidence establishes that signals with g ca. 2·01 and 2·005 are those of sulphinyl (RSO˙) and sulphonyl (RSO₂˙) radicals, respectively. Radicals of both these types are detected in almost all instances; thiyl radicals (RS˙) cannot be detected directly but their involvement is demonstrated by spin-trapping methods; and two dithiols yield spectra with g ca. 2·013 which are attributed to cyclic disulphide radical-anions. Reaction mechanisms consistent with the e.s.r. data and earlier product studies are suggested.

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DOI: https://doi.org/10.1039/P29750000892
Article type: Paper

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J. Chem. Soc., Perkin Trans. 2, 1975, 892-900

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Electron spin resonance studies. Part XLVI. Oxidation of thiols and disulphides in aqueous solution: formation of RS˙, RSO˙, RSO₂˙, RSSR^–, and carbon radicals

B. C. Gilbert, H. A. H. Laue, R. O. C. Norman and R. C. Sealy, J. Chem. Soc., Perkin Trans. 2, 1975, 892 DOI: 10.1039/P29750000892

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Journal of the Chemical Society, Perkin Transactions 2