An investigation of the intramolecular hydrogen bonds in several substituted phenols containing the CF3 group

Konovalov, E. V.; Egorov, Yu. P.; Belinskaya, R. V.; Boiko, V. N.; Yagupol’skii, L. M.

doi:10.1007/bf00606044

Cited by 1 publication

(1 citation statement)

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“…39 Our recent theoretical study of 2-trifluoromethylphenol 40 (1) found weak intramolecular hydrogen bonding accompanied by characteristic changes in the geometry of the rest of the molecule, compared with the structures of the parent phenol and trifluoromethylbenzene. In agreement with available experimental results [41][42][43][44] the ab initio calculations predicted the hydrogen-bonded syn conformer (Chart 1) to be more stable than the anti form in which the hydroxy hydrogen points away from the CF 3 group. At the MP2/6-31+G**//MP2/6-31G** level, corrected for zero-point Vibrational energy, the energy difference is 7.65 kJ/mol.…”

Section: Introductionsupporting

confidence: 84%

Bifurcated Hydrogen Bonding in 2-Trifluoromethylphenol Confirmed by Gas Electron Diffraction

Kovács

Hargittai

1998

J. Phys. Chem. A

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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 (r g) 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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Section: Introductionsupporting

confidence: 84%