Andrea A. Kovacs, I. Hargittai
Apr 22, 1998
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Influential Citations
8
Citations
Journal
Journal of Physical Chemistry A
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 A; C−C(F3), 1.510 ± 0.005 A; C−O, 1.362 ± 0.011 A; (C−F)mean, 1.358 ± 0.006 A; ∠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 A. Compared with the freely rotating CF3 group in trifluoromethylbenzene, the well-defined conformer of 2-trifluoromethylphenol indicates the constraining effect of hydrogen bonding.