Bifurcated hydrogen bonding in 2-trifluoromethylphenol confirmed by gas electron diffraction

Attila Kovács, I. Hargittai

Research output: Contribution to journalArticle

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Abstract

The molecular structure of 2-trifluoromethylphenol has been determined by gas-phase electron diffraction. The analysis, aided by constraints from ab initio molecular orbital calculations, yielded the following bond lengths (rg) and bond angles: (C-C)Ar,mean, 1.395 ± 0.004 Å; C-C(F3), 1.510 ± 0.005 Å; C-O, 1.362 ± 0.011 Å; (C-F)mean, 1.358 ± 0.006 Å; 〈O-C1-C2, 121.0 ± 1.2°; 〈C-O-H, 105 ± 6°; 〈C(F3)-C2-C1, 120.7 ± 0.8°; (C-C-F)mean, 113.2 ± 0.3°; CF3 torsion, 10.1 ± 0.8°. Weak intramolecular bifurcated hydrogen bonding between the hydroxy hydrogen and two of the CF3 fluorines is indicated by the H⋯F nonbonded distances 2.05 ± 0.06 and 2.42 ± 0.06 Å. Compared with the freely rotating CF3 group in trifluoromethylbenzene, the well-defined conformer of 2-trifluoromethylphenol indicates the constraining effect of hydrogen bonding.

Original languageEnglish
Pages (from-to)3415-3419
Number of pages5
JournalJournal of Physical Chemistry A
Volume102
Issue number19
Publication statusPublished - May 7 1998

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Electron diffraction
Hydrogen bonds
electron diffraction
Orbital calculations
Fluorine
Bond length
Molecular orbitals
hydrogen
gases
Torsional stress
Molecular structure
Hydrogen
Gases
torsion
fluorine
molecular orbitals
molecular structure
vapor phases
2-trifluoromethylphenol
benzotrifluoride

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

Bifurcated hydrogen bonding in 2-trifluoromethylphenol confirmed by gas electron diffraction. / Kovács, Attila; Hargittai, I.

In: Journal of Physical Chemistry A, Vol. 102, No. 19, 07.05.1998, p. 3415-3419.

Research output: Contribution to journalArticle

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abstract = "The molecular structure of 2-trifluoromethylphenol has been determined by gas-phase electron diffraction. The analysis, aided by constraints from ab initio molecular orbital calculations, yielded the following bond lengths (rg) and bond angles: (C-C)Ar,mean, 1.395 ± 0.004 {\AA}; C-C(F3), 1.510 ± 0.005 {\AA}; C-O, 1.362 ± 0.011 {\AA}; (C-F)mean, 1.358 ± 0.006 {\AA}; 〈O-C1-C2, 121.0 ± 1.2°; 〈C-O-H, 105 ± 6°; 〈C(F3)-C2-C1, 120.7 ± 0.8°; (C-C-F)mean, 113.2 ± 0.3°; CF3 torsion, 10.1 ± 0.8°. Weak intramolecular bifurcated hydrogen bonding between the hydroxy hydrogen and two of the CF3 fluorines is indicated by the H⋯F nonbonded distances 2.05 ± 0.06 and 2.42 ± 0.06 {\AA}. Compared with the freely rotating CF3 group in trifluoromethylbenzene, the well-defined conformer of 2-trifluoromethylphenol indicates the constraining effect of hydrogen bonding.",
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N2 - The molecular structure of 2-trifluoromethylphenol has been determined by gas-phase electron diffraction. The analysis, aided by constraints from ab initio molecular orbital calculations, yielded the following bond lengths (rg) and bond angles: (C-C)Ar,mean, 1.395 ± 0.004 Å; C-C(F3), 1.510 ± 0.005 Å; C-O, 1.362 ± 0.011 Å; (C-F)mean, 1.358 ± 0.006 Å; 〈O-C1-C2, 121.0 ± 1.2°; 〈C-O-H, 105 ± 6°; 〈C(F3)-C2-C1, 120.7 ± 0.8°; (C-C-F)mean, 113.2 ± 0.3°; CF3 torsion, 10.1 ± 0.8°. Weak intramolecular bifurcated hydrogen bonding between the hydroxy hydrogen and two of the CF3 fluorines is indicated by the H⋯F nonbonded distances 2.05 ± 0.06 and 2.42 ± 0.06 Å. Compared with the freely rotating CF3 group in trifluoromethylbenzene, the well-defined conformer of 2-trifluoromethylphenol indicates the constraining effect of hydrogen bonding.

AB - The molecular structure of 2-trifluoromethylphenol has been determined by gas-phase electron diffraction. The analysis, aided by constraints from ab initio molecular orbital calculations, yielded the following bond lengths (rg) and bond angles: (C-C)Ar,mean, 1.395 ± 0.004 Å; C-C(F3), 1.510 ± 0.005 Å; C-O, 1.362 ± 0.011 Å; (C-F)mean, 1.358 ± 0.006 Å; 〈O-C1-C2, 121.0 ± 1.2°; 〈C-O-H, 105 ± 6°; 〈C(F3)-C2-C1, 120.7 ± 0.8°; (C-C-F)mean, 113.2 ± 0.3°; CF3 torsion, 10.1 ± 0.8°. Weak intramolecular bifurcated hydrogen bonding between the hydroxy hydrogen and two of the CF3 fluorines is indicated by the H⋯F nonbonded distances 2.05 ± 0.06 and 2.42 ± 0.06 Å. Compared with the freely rotating CF3 group in trifluoromethylbenzene, the well-defined conformer of 2-trifluoromethylphenol indicates the constraining effect of hydrogen bonding.

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