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Experimental and theoretical investigation of NMR 2 J HH coupling constant on six‐membered ring systems containing oxygen or sulfur atoms
Author(s) -
Tormena Cláudio F.,
Vilcachagua Janaína D.,
Karcher Viviane,
Rittner Roberto,
Contreras Rubén H.
Publication year - 2007
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2014
Subject(s) - chemistry , geminal , coupling constant , antibonding molecular orbital , cyclohexane , sulfur , ring (chemistry) , oxygen , coupling (piping) , computational chemistry , crystallography , oxygen 17 , stereochemistry , atomic physics , atomic orbital , organic chemistry , physics , quantum mechanics , electron , mechanical engineering , engineering
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.