The Polar Hydrophobicity of Fluorinated Compounds

Justin C. Biffinger; Hong Woo Kim; Stephen G. DiMagno

doi:10.1002/cbic.200300910

Abstract

Fluorine's peculiar property: The CF 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.

Keywords

PolarFluorineChemical polarityPolarity (international relations)SchematicChemistryDipoleRepresentation (politics)Computational chemistryChemical physicsProperty (philosophy)Organic chemistryCombinatorial chemistryMaterials sciencePhysicsBiochemistry

Affiliated Institutions

University of Nebraska–Lincoln US

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Publication Info

Year: 2004
Type: review
Volume: 5
Issue: 5
Pages: 622-627
Citations: 462
Access: Closed

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APA Style

                            
                                    Justin C. Biffinger, 
                                
                                    Hong Woo Kim, 
                                
                                    Stephen G. DiMagno
                                
                            (2004). 
                            The Polar Hydrophobicity of Fluorinated Compounds. 
                            ChemBioChem
                            , 5
                            (5)
                            , 622-627.
                            https://doi.org/10.1002/cbic.200300910

Identifiers

DOI: 10.1002/cbic.200300910