Conformational preferences for 1,2- and 1,4-difluorocyclohexane

Kenneth B. Wiberg; Wolfgang Hinz; Ronald M. Jarret; Katherine B. Aubrecht

doi:10.1021/jo051049w

Conformational preferences for 1,2- and 1,4-difluorocyclohexane

Kenneth B. Wiberg
, Wolfgang Hinz
, Ronald M. Jarret
, Katherine B. Aubrecht

Chemistry

Yale University
College of the Holy Cross

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

21 Scopus citations

Abstract

The conformational preference for 1,2-difluorocyclohexane has been studied experimentally via NMR spectroscopy and computationally using CCSD/6-311+G(2df,p). The results confirm our previous conclusions that the diaxial conformer of trans-1,2-difluorocyclohexane has the lower energy in the gas phase, whereas the diequatorial conformer has the lower energy in solution. SCIPCM reaction field calculations reproduce the observed solvent effects. The 1,4-difluorocyclohexanes have also been reexamined computationally.

Original language	English
Pages (from-to)	8381-8384
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	70
Issue number	21
DOIs	https://doi.org/10.1021/jo051049w
State	Published - Oct 14 2005

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title = "Conformational preferences for 1,2- and 1,4-difluorocyclohexane",

abstract = "The conformational preference for 1,2-difluorocyclohexane has been studied experimentally via NMR spectroscopy and computationally using CCSD/6-311+G(2df,p). The results confirm our previous conclusions that the diaxial conformer of trans-1,2-difluorocyclohexane has the lower energy in the gas phase, whereas the diequatorial conformer has the lower energy in solution. SCIPCM reaction field calculations reproduce the observed solvent effects. The 1,4-difluorocyclohexanes have also been reexamined computationally.",

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AU - Wiberg, Kenneth B.

AU - Hinz, Wolfgang

AU - Jarret, Ronald M.

AU - Aubrecht, Katherine B.

PY - 2005/10/14

Y1 - 2005/10/14

N2 - The conformational preference for 1,2-difluorocyclohexane has been studied experimentally via NMR spectroscopy and computationally using CCSD/6-311+G(2df,p). The results confirm our previous conclusions that the diaxial conformer of trans-1,2-difluorocyclohexane has the lower energy in the gas phase, whereas the diequatorial conformer has the lower energy in solution. SCIPCM reaction field calculations reproduce the observed solvent effects. The 1,4-difluorocyclohexanes have also been reexamined computationally.

AB - The conformational preference for 1,2-difluorocyclohexane has been studied experimentally via NMR spectroscopy and computationally using CCSD/6-311+G(2df,p). The results confirm our previous conclusions that the diaxial conformer of trans-1,2-difluorocyclohexane has the lower energy in the gas phase, whereas the diequatorial conformer has the lower energy in solution. SCIPCM reaction field calculations reproduce the observed solvent effects. The 1,4-difluorocyclohexanes have also been reexamined computationally.

UR - https://www.scopus.com/pages/publications/26844449316

U2 - 10.1021/jo051049w

DO - 10.1021/jo051049w

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

Conformational preferences for 1,2- and 1,4-difluorocyclohexane

Abstract

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