Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols
2012 ◽
Vol 8
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pp. 1227-1232
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Keyword(s):
Four diastereoisomers of 2-fluorobicyclo[2.2.1]heptan-7-ols were computationally investigated by using quantum-chemical calculations, and their relative energies were analyzed on the basis of stereoelectronic interactions, particularly the presence or otherwise of the F∙∙∙HO intramolecular hydrogen bond in the syn-exo isomer. It was found through NBO and AIM analyses that such an interaction contributes to structural stabilization and that the 1h J F,H(O) coupling constant in the syn-exo isomer is modulated by the n F→σ*OH interaction, i.e., the quantum nature of the F∙∙∙HO hydrogen bond.
2004 ◽
Vol 108
(8)
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pp. 1403-1408
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1998 ◽
Vol 452
(1-3)
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pp. 185-202
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2013 ◽
Vol 9
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pp. 1127-1134
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2019 ◽
Vol 217
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pp. 8-12
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2013 ◽
Vol 1012
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pp. 20-26
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1993 ◽
Vol 33
(5)
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pp. 636-643
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