Oxygen-17 nuclear magnetic resonance spectroscopy of sulfoxides and sulfones. Alkyl substituent induced chemical shift effects

Journal Article · Fri Sep 10 00:00:00 EDT 1982 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00140a014· OSTI ID:6628958

Dyer, J C; Harris, D L; Evans, Jr, S A

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 /sup 17/O NMR chemical shifts for the acyclic, aliphatic, and aromatic sulfoxides reported here absorb in the narrow range between delta -20 and +20, while the cyclic, aliphatic sulfoxides absorb between delta -13 and +66 relative to external (but naturally abundant) H/sub 2//sup 17/O. The sulfonyl oxygens are deshielded relative to the sulfinyl oxygens, exhibiting chemical shifts for acyclic and cyclic sulfonyl oxygens between delta 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.

• Research Organization: Univ. of North Carolina, Chapel Hill
• DOE Contract Number: AS05-80ER10641
• OSTI ID: 6628958
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 47:19; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
AROMATICS
CHEMICAL SHIFT
DATA
EVEN-ODD NUCLEI
EXPERIMENTAL DATA
INFORMATION
ISOTOPES
LIGHT NUCLEI
MAGNETIC RESONANCE
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
OXYGEN 17
OXYGEN ISOTOPES
RESONANCE
SPECTROSCOPY
STABLE ISOTOPES
SULFONES
SULFOXIDES