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.

SUBMITTER: de Rezende FM 

PROVIDER: S-EPMC3458742 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature