The polar hydrophobicity of fluorinated compounds

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

Research output: Contribution to journalShort survey

328 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 languageEnglish (US)
Pages (from-to)622-627
Number of pages6
JournalChemBioChem
Volume5
Issue number5
DOIs
StatePublished - May 3 2004

Keywords

  • Carbohydrates
  • Enzyme inhibitors
  • Fluorine
  • Hydrogen bonds
  • Hydrophobic interactions

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry

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  • Cite this

    Biffinger, J. C., Kim, H. W., & DiMagno, S. G. (2004). The polar hydrophobicity of fluorinated compounds. ChemBioChem, 5(5), 622-627. https://doi.org/10.1002/cbic.200300910