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Type: Artigo de periódico
Title: Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols
Author: de Rezende, FMP
Moreira, MA
Cormanich, RA
Freitas, MP
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 center dot center dot center dot 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)->sigma*(OH) interaction, i.e., the quantum nature of the F center dot center dot center dot HO hydrogen bond.
Subject: conformational analysis
hydrogen bond
(1h)J(F,H(O)) coupling constant
quantum-chemical calculations
Country: Alemanha
Editor: Beilstein-institut
Rights: aberto
Identifier DOI: 10.3762/bjoc.8.137
Date Issue: 2012
Appears in Collections:Unicamp - Artigos e Outros Documentos

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