Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols

• Autor(a) principal: Rezende, Fátima M. P. de
• Data de Publicação: 2012
• Outros Autores: Moreira, Marilua A., Cormanich, Rodrigo A., Freitas, Matheus P.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Institucional da UFLA
• Texto Completo: http://repositorio.ufla.br/jspui/handle/1/41823
• topic: Conformational analysis; 2-fluorobicyclo[2.2.1]heptan-7-ols; Hydrogen bond; 1hJF,H(O) coupling constant; Quantum-chemical calculations

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.