Experimental and theoretical investigation of NMR 2JHH coupling constant on six-membered ring systems containing oxygen or sulfur atoms
✍ Scribed by Cláudio F. Tormena; Janaína D. Vilcachagua; Viviane Karcher; Roberto Rittner; Rubén H. Contreras
- Publisher
- John Wiley and Sons
- Year
- 2007
- Tongue
- English
- Weight
- 129 KB
- Volume
- 45
- Category
- Article
- ISSN
- 0749-1581
- DOI
- 10.1002/mrc.2014
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✦ Synopsis
Abstract
Theoretical and experimental ^2^J~HH~ coupling constants for six‐membered rings containing oxygen or sulfur atoms were studied to investigate whether the ^2^J~HH~ coupling constant can be used for stereoelectronic studies in heterocyclohexanes, instead of ^1^J~CH~, because it is well known that experimental measurements of ^2^J~HH~ coupling constants at low temperature are much easier to determine than the corresponding ^1^J~CH~ couplings. For all compounds studied here, the ^2^J~HH~ coupling constants are affected by σ*~C–H~ antibonding occupancy together with bond angle effects. For cyclohexane and oxygen‐containing compounds, the influence on the geminal coupling for H~ax~‐C~2~‐H~eq~ and for X~1~‐C~2~‐X~3~ (X = O and C), bond angles are more pronounced than for the sulfur derivatives. Copyright © 2007 John Wiley & Sons, Ltd.