The F?HO intramolecular hydrogen bond forming five-membered rings hardly appear in monocyclic organofluorine compounds?

RSC Advances Pub Date: 2012-03-05 DOI: 10.1039/C2RA00039C

Abstract

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[double bond, length as m-dash]C(F)–C(OH)[double bond, length as m-dash]C fragments, predict that the F?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?HO intramolecular H-bond.

Graphical abstract: The F?HO intramolecular hydrogen bond forming five-membered rings hardly appear in monocyclic organofluorine compounds
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