Oxygen-17 Nuclear Magnetic Resonance Spectroscopy of Sulfoxides and Sulfones. Alkyl Substituent Induced Chemical Shift Effects.

Article abstract of DOI:10.1021/jo00140a014

Oxygen-17 NMR chemical shifts have been determined for a number of cyclic and acyclic as well as aliphatic, olefinic, and aryl sulfoxides and sulfones.The (17)O NMR chemical shifts for the acyclic, aliphatic, and aromatic sulfoxides reported here absorb in the narrow range between δ -20 and +20, while the cyclic, aliphatic sulfoxides absorb between δ -13 and +66 relative to external (but naturally abundant) H2(17)O.The sulfonyl oxygens are deshielded relative to sulfinyl oxygens, exhibiting chemical shifts for acyclic and cyclic sulfonyl oxygens between δ 120 and 183 for the sulfones reported here.Diastereotopic sulfonyl oxygens exhibit chemical shift nonequivalence.Substituent-induced chemical shift effects by a methyl or methylene group on the sulfinyl and sulfonyl oxygens are discussed.