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The Polar Hydrophobicity of Fluorinated Compounds
Abstract
Fluorine's peculiar property: The CF bond is marked by a peculiar combination of polarity on nonpolarizability (hardness); this imbues fluorinated compounds with polar hydrophobicity. This property, whereby desolvation of fluorinated surfaces and weak dipolar interactions in organized media drive molecular recognition (see schematic representation), is argued to be a useful design principle and a likely explanation for the abundance of fluorinated compounds in medicinal chemistry.
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Cited by
De Silva, A. O., Armitage, J. M., Bruton, T. A., Dassuncao, C., Heiger-Bernays, W., Hu, X. C., Kärrman, A., Kelly, B., Ng, C., Robuck, A., et al. (2020) · Environmental Toxicology and Chemistry · doi:10.1002/etc.4935 · Cited by 835
Halogen atoms in the modern medicinal chemistry: hints for the drug design
Hernandes, M., Cavalcanti, S. M., Moreira, D. R., de Azevedo Junior, W., & Leite, A. C. (2010) · Current Drug Targets · doi:10.2174/138945010790711996 · Cited by 723
Molecular origins of fluorocarbon hydrophobicity
Dalvi, V. H., & Rossky, P. J. (2010) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0915169107 · Cited by 421
Physicochemical properties and aquatic toxicity of poly- and Perfluorinated compounds
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Temporal and Fluoride Control of Secondary Metabolism Regulates Cellular Organofluorine Biosynthesis
Walker, M. C., Wen, M., Weeks, A. M., & Chang, M. C. Y. (2012) · ACS Chemical Biology · doi:10.1021/cb3002057 · Cited by 21
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Metadata
- Authors
- Biffinger, J. C., Kim, H. W., & DiMagno, S. G.
- Venue
- ChemBioChem
- Publisher
- Wiley
- Published
- 2004-04-28
- Volume
- 5
- Issue
- 5
- Pages
- 622-627
- ISSN
- 1439-4227 (ISSN-L)
- 1439-7633
- OpenAlex
- W2159065552
- Cited by
- 486
- References
- 1
- FWCI
- 9.97
- Type
- journal article
- Language
- en
- Open access
- closed
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