Synthesis and charge density determination of 4,4-difluoro-3,5-diphenyl-4H-pyrazole and a hydrate derivative

Leann Walton, Holly R. Duplain, Allyson L. Knapp, Cheryl K. Eidell, John Bacsa, Chad E. Stephens

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Abstract

We describe the synthesis of the title gem-difluoropyrazole and hydrate derivative by reaction of 3,5-diphenylpyrazole with the NF reagent Selectfluor. In addition to spectral characterization of the two products, X-ray crystal structures were determined and an analysis of the charge densities of each compound was carried out. It is proposed that a weakened NN bond in the parent pyrazole, perhaps a result of the gem-difluoro substitution, promotes formation of the hydrate. The title gem-difluoropyrazole is a potential precursor to gem-difluorinated cyclopropanes.

Original languageEnglish (US)
Pages (from-to)470-480
Number of pages11
JournalJournal of Fluorine Chemistry
Volume173
DOIs
StatePublished - May 2015

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Keywords

  • Density functional theory (DFT)
  • Fluorination
  • Pyrazole
  • Selectfluor
  • X-ray crystallography

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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