Artículos de revistas
The F center dot center dot center dot HO intramolecular hydrogen bond forming five-membered rings hardly appear in monocyclic organofluorine compounds
Registro en:
Rsc Advances. Royal Soc Chemistry, v. 2, n. 10, n. 4169, n. 4174, 2012.
2046-2069
WOS:000304327300023
10.1039/c2ra00039c
Autor
Cormanich, RA
Freitas, MP
Tormena, CF
Rittner, R
Institución
Resumen
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) This paper emphasizes that fluorine atoms in organic molecules need special geometric requirements to experience intramolecular hydrogen bonds (H-bonds). Calculations at the B3LYP/aug-cc-pVDZ theoretical level and using the quantum theory of atoms in molecules applied over a series of monocyclic compounds, which have similar C = C(F)-C(OH)= C fragments, predict that the F center dot center dot center dot HO intramolecular H-bond does not exist when forming five-membered rings. Indeed, it is shown that the geometric restrictions imposed by the rigid rings are the main reasons in preventing fluorine participating in such a F center dot center dot center dot HO intramolecular H-bond. 2 10 4169 4174 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)