Understanding organofluorine chemistry. An introduction to the C-F bond

Chemical Society Reviews
David O'Hagan

Abstract

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.

References

May 16, 1998·Nature·S K HolmgrenR T Raines
Feb 27, 2004·Organic & Biomolecular Chemistry·Caroline R S BriggsJudith A K Howard
May 4, 2004·Chembiochem : a European Journal of Chemical Biology·Justin C BiffingerStephen G DiMagno
May 4, 2004·Chembiochem : a European Journal of Chemical Biology·Herbert Plenio
Jul 15, 2004·Chemistry : a European Journal·Isabella Hyla-KryspinStefan Grimme
Dec 4, 2004·The Journal of Organic Chemistry·Cara L JenkinsGrant R Krow
Jan 22, 2005·Chemistry : a European Journal·Aiming SunJames P Snyder
Apr 27, 2005·Chemical Society Reviews·Ronald J Gillespie, Edward A Robinson
Oct 8, 2005·The Journal of Organic Chemistry·Kenneth B WibergKatherine B Aubrecht
Feb 25, 2006·The Journal of Organic Chemistry·Thomas X CarrollLeif J Saethre
Jul 13, 2006·The Journal of Physical Chemistry. a·Lionel GoodmanVojislava Pophristic
Aug 22, 2006·Current Topics in Medicinal Chemistry·Stephen G Dimagno, Haoran Sun
Sep 7, 2006·Journal of the American Chemical Society·Tobias RitterRobert H Grubbs
Oct 5, 2006·Journal of the American Chemical Society·Gerry A GriffithMark A Vincent
Oct 19, 2006·Chemical Communications : Chem Comm·Eric T Kool, Herman O Sintim
Apr 5, 2007·Organic & Biomolecular Chemistry·Samuel Couve-BonnaireXavier Pannecoucke
May 29, 2007·ChemMedChem·Martin MorgenthalerKlaus Müller
Jul 5, 2007·Angewandte Chemie·Natalie E J GoosemanRobert J Young
Sep 6, 2007·Angewandte Chemie·Luke HunterDavid O'Hagan

❮ Previous
Next ❯

Citations

Apr 5, 2011·Chemical Reviews·Olesya A Tomashenko, Vladimir V Grushin
Aug 11, 2010·Journal of the American Chemical Society·Pingping TangTobias Ritter
Apr 23, 2011·Journal of the American Chemical Society·Peter W Y ChanEmil F Pai
Jul 9, 2011·Journal of the American Chemical Society·Pingping TangTobias Ritter
Mar 31, 2012·Journal of the American Chemical Society·Christopher D BrownLaura L Kiessling
Oct 16, 2012·Journal of the American Chemical Society·Eunsung LeeTobias Ritter
Mar 19, 2011·Journal of Medicinal Chemistry·Nicholas A Meanwell
Apr 21, 2011·Journal of Medicinal Chemistry·Stephen D Roughley, Allan M Jordan
Jun 29, 2013·Journal of Medicinal Chemistry·Kai SeehaferChristian D Klein
Sep 26, 2012·The Journal of Organic Chemistry·Rakesh Kumar, Barbara Zajc
May 27, 2011·Nature·Takeru FuruyaTobias Ritter
Aug 9, 2008·Chemical Communications : Chem Comm·Tomas GustafssonPeter H Seeberger
Jul 31, 2008·Chemical Communications : Chem Comm·Sophie BoldonVéronique Gouverneur
Sep 20, 2008·Chemical Communications : Chem Comm·Henri RudlerJean-Claude Daran
Sep 24, 2009·Chemical Communications : Chem Comm·Per RestorpJulius Rebek
Jun 29, 2011·Chemical Communications : Chem Comm·Alastair J DurieDavid O'Hagan
Aug 6, 2011·Chemical Communications : Chem Comm·Anja Hoffmann-Röder, Manuel Johannes
Sep 15, 2011·Chemical Communications : Chem Comm·Avgousta IoannouBruno Linclau
Feb 16, 2012·Chemical Communications : Chem Comm·Charlotte Hollingworth, Véronique Gouverneur
Jan 10, 2012·Chemical Communications : Chem Comm·Yun-Lin Liu, Jian Zhou
Feb 22, 2012·Organic & Biomolecular Chemistry·Samir K MandalBarbara Zajc
Apr 13, 2011·The Journal of Biological Chemistry·Matthew D Shoulders, Ronald T Raines
Mar 6, 2010·Acta Crystallographica. Section C, Crystal Structure Communications·Simone DedolaRobert A Field
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Michael T KirchnerGautam R Desiraju
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Michael T KirchnerGautam R Desiraju
Apr 6, 2013·Science·Ulrich Hennecke
Jan 5, 2013·Nanoscale Research Letters·Sahng-Kyoon JerngSeung-Hyun Chun
Oct 23, 2008·Beilstein Journal of Organic Chemistry·David O'Hagan
Oct 23, 2008·Beilstein Journal of Organic Chemistry·Takehisa IshimaruTakeshi Toru
Jan 1, 2009·Beilstein Journal of Organic Chemistry·Vincent A BrunetDavid O'Hagan
May 27, 2010·Beilstein Journal of Organic Chemistry·Luke Hunter
May 27, 2010·Beilstein Journal of Organic Chemistry·Guillaume G LaunayDavid O'Hagan

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Chemical Society Reviews
Sophie PurserVéronique Gouverneur
Chembiochem : a European Journal of Chemical Biology
Justin C BiffingerStephen G DiMagno
© 2021 Meta ULC. All rights reserved