Skip to main page content
Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
, 37 (2), 308-19

Understanding Organofluorine Chemistry. An Introduction to the C-F Bond


Understanding Organofluorine Chemistry. An Introduction to the C-F Bond

David O'Hagan. Chem Soc Rev.


Fluorine is the most electronegative element in the periodic table. When bound to carbon it forms the strongest bonds in organic chemistry and this makes fluorine substitution attractive for the development of pharmaceuticals and a wide range of speciality materials. Although highly polarised, the C-F bond gains stability from the resultant electrostatic attraction between the polarised C delta+ and F delta- atoms. This polarity suppresses lone pair donation from fluorine and in general fluorine is a weak coordinator. However, the C-F bond has interesting properties which can be understood either in terms of electrostatic/dipole interactions or by considering stereoelectronic interactions with neighbouring bonds or lone pairs. In this tutorial review these fundamental aspects of the C-F bond are explored to rationalise the geometry, conformation and reactivity of individual organofluorine compounds.

Similar articles

See all similar articles

Cited by 185 articles

See all "Cited by" articles

LinkOut - more resources