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Stereoelectronic Effects: The γ-Gauche Effect in Sulfoxides.

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The sulfoxide γ-gauche effect in carbon-13 NMR spectroscopy is caused by stereoelectronic interactions, specifically the sulfur lone pair. This effect is not due to steric factors.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Spectroscopy

Background:

  • The 13C NMR gamma-gauche effect describes shielding of carbons beta to a sulfoxide group.
  • Previous explanations often cited steric interactions.

Purpose of the Study:

  • Investigate the origins of the 13C NMR gamma-gauche effect in sulfoxides.
  • Clarify the role of stereoelectronic versus steric factors.

Main Methods:

  • Calculated and measured 13C NMR data for various sulfoxides.
  • Iso-chemical-shielding surfaces (ICSSs) and current maps.
  • Natural Bond Orbital (NBO) and Natural Chemical Shielding (NCS) analyses.

Main Results:

  • Upfield shifts occur only when the beta-carbon is anti to the sulfur lone pair.
  • Carbons synclinal to the lone pair are unaffected.
  • The S=O bond can be described as a reduced triple bond.

Conclusions:

  • The gamma-gauche effect is primarily due to stereoelectronic interactions, particularly the sulfur lone pair.
  • Steric interactions do not adequately explain the observed shielding.
  • The bonding in sulfoxides involves significant antibonding contributions.