Abstract
AbstractComputational and experimental evidence that participation of a remote heteroatom occurs during the formation and decomposition of persulfoxides is presented. The experimental ramifications of remote participation includes a dramatic increase in the rate of reaction with singlet oxygen and a decrease in the conformationally dependent ability of sulfides to physically deactivate singlet oxygen. The ability of different heteroatoms to participate is evaluated with a natural bond orbital analysis, and a comparison of the extent of participation in persulfoxides and their homologous sulfoxides is presented. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:591–599, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20343
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