The polar hydrophobicity of fluorinated compounds

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

doi:10.1002/cbic.200300910

The polar hydrophobicity of fluorinated compounds

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

Research output: Contribution to journal › Short survey › peer-review

413 Scopus citations

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.

Original language	English (US)
Pages (from-to)	622-627
Number of pages	6
Journal	ChemBioChem
Volume	5
Issue number	5
DOIs	https://doi.org/10.1002/cbic.200300910
State	Published - May 3 2004
Externally published	Yes

Keywords

Carbohydrates
Enzyme inhibitors
Fluorine
Hydrogen bonds
Hydrophobic interactions

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Organic Chemistry

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10.1002/cbic.200300910

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AU - Kim, Hong Woo

AU - DiMagno, Stephen G.

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N2 - 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.

AB - 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.

KW - Carbohydrates

KW - Enzyme inhibitors

KW - Fluorine

KW - Hydrogen bonds

KW - Hydrophobic interactions

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The polar hydrophobicity of fluorinated compounds

Abstract

Keywords

ASJC Scopus subject areas

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