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

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...

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Autores principales: de Rezende, Fátima M P, Moreira, Marilua A, Cormanich, Rodrigo A, Freitas, Matheus P
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458742/
https://www.ncbi.nlm.nih.gov/pubmed/23019452
http://dx.doi.org/10.3762/bjoc.8.137
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author de Rezende, Fátima M P
Moreira, Marilua A
Cormanich, Rodrigo A
Freitas, Matheus P
author_facet de Rezende, Fátima M P
Moreira, Marilua A
Cormanich, Rodrigo A
Freitas, Matheus P
author_sort de Rezende, Fátima M P
collection PubMed
description 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.
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spelling pubmed-34587422012-09-27 Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols de Rezende, Fátima M P Moreira, Marilua A Cormanich, Rodrigo A Freitas, Matheus P Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2012-08-02 /pmc/articles/PMC3458742/ /pubmed/23019452 http://dx.doi.org/10.3762/bjoc.8.137 Text en Copyright © 2012, de Rezende et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
de Rezende, Fátima M P
Moreira, Marilua A
Cormanich, Rodrigo A
Freitas, Matheus P
Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols
title Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols
title_full Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols
title_fullStr Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols
title_full_unstemmed Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols
title_short Conformational analysis, stereoelectronic interactions and NMR properties of 2-fluorobicyclo[2.2.1]heptan-7-ols
title_sort conformational analysis, stereoelectronic interactions and nmr properties of 2-fluorobicyclo[2.2.1]heptan-7-ols
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458742/
https://www.ncbi.nlm.nih.gov/pubmed/23019452
http://dx.doi.org/10.3762/bjoc.8.137
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