1. Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols
- Author
-
Matheus P. Freitas, Rodrigo A. Cormanich, Marilua A. Moreira, and Fátima M.P. de Rezende
- Subjects
Coupling constant ,hydrogen bond ,Chemistry ,Stereochemistry ,Hydrogen bond ,Organic Chemistry ,Diastereomer ,conformational analysis ,quantum-chemical calculations ,1hJF,H(O) coupling constant ,Full Research Paper ,lcsh:QD241-441 ,lcsh:Organic chemistry ,Computational chemistry ,Intramolecular force ,2-fluorobicyclo[2.2.1]heptan-7-ols ,lcsh:Q ,lcsh:Science ,Quantum ,Natural bond orbital - 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 1hJF,H(O) coupling constant in the syn-exo isomer is modulated by the nF→σ*OH interaction, i.e., the quantum nature of the F∙∙∙HO hydrogen bond.
- Published
- 2012