title: Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols.
abstract: 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.
authors.affiliation: Department of Chemistry, Federal University of Lavras, P.O. Box 3037, 37200-000, Lavras, MG, Brazil.
authors.forename: Fátima M P
authors.initials: FM
authors.lastname: de Rezende
authors.forename: Marilua A
authors.initials: MA
authors.lastname: Moreira
authors.forename: Rodrigo A
authors.initials: RA
authors.lastname: Cormanich
authors.forename: Matheus P
authors.initials: MP
authors.lastname: Freitas