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

doi:10.1016/j.jfluchem.2015.01.003

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

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

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 language	English (US)
Pages (from-to)	470-480
Number of pages	11
Journal	Journal of Fluorine Chemistry
Volume	173
DOIs	https://doi.org/10.1016/j.jfluchem.2015.01.003
State	Published - May 2015

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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10.1016/j.jfluchem.2015.01.003

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

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.",

keywords = "Density functional theory (DFT), Fluorination, Pyrazole, Selectfluor, X-ray crystallography",

author = "Leann Walton and Duplain, {Holly R.} and Knapp, {Allyson L.} and Eidell, {Cheryl K.} and John Bacsa and Stephens, {Chad E.}",

note = "Funding Information: The authors acknowledge the Department of Chemistry and Physics at GRU for partial funding of this research and the resources of the Cherry L. Emerson Center for Scientific Computation at Emory University. Publisher Copyright: {\textcopyright} 2015 Elsevier B.V. All rights reserved.",

year = "2015",

month = may,

doi = "10.1016/j.jfluchem.2015.01.003",

language = "English (US)",

volume = "173",

pages = "470--480",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier BV",

}

TY - JOUR

T1 - Synthesis and charge density determination of 4,4-difluoro-3,5-diphenyl-4H-pyrazole and a hydrate derivative

AU - Walton, Leann

AU - Duplain, Holly R.

AU - Knapp, Allyson L.

AU - Eidell, Cheryl K.

AU - Bacsa, John

AU - Stephens, Chad E.

N1 - Funding Information: The authors acknowledge the Department of Chemistry and Physics at GRU for partial funding of this research and the resources of the Cherry L. Emerson Center for Scientific Computation at Emory University. Publisher Copyright: © 2015 Elsevier B.V. All rights reserved.

PY - 2015/5

Y1 - 2015/5

N2 - 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.

AB - 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.

KW - Density functional theory (DFT)

KW - Fluorination

KW - Pyrazole

KW - Selectfluor

KW - X-ray crystallography

UR - http://www.scopus.com/inward/record.url?scp=84923640181&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84923640181&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2015.01.003

DO - 10.1016/j.jfluchem.2015.01.003

M3 - Article

AN - SCOPUS:84923640181

SN - 0022-1139

VL - 173

SP - 470

EP - 480

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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