Molecular structure of tetrafluorohydroquinone and geometrical indication of intramolecular hydrogen bonding from gas-phase electron diffraction

Erzsébet Vajda, István Hargittai

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Abstract

The molecular structure of tetrafluorohydroquinone has been determined by electron diffraction in the gas phase. The molecular geometry indicates possible formation of a weak intramolecular hydrogen bond between the OH and F substituents in ortho positions. The nearest H⋯F and O⋯F interactions, at 2.02 ± 0.07 and 2.66 ± 0.05 Å, are closer than the sums of van der Waals radii, 2.55 and 2.75 Å, respectively. The C-OH and C-F bonds are somewhat tilted towards each other. The C-O-H angle, 98 ± 2°, is smaller than in hydroquinone. The C-O bond, (rg), 1.353 ± 0.009 Å, is shorter than in phenol and in hydroquinone. The ring parameters are rg(C-C)mean 1.394 ± 0.003 Å, 〈C-C(OH)-C = 117.0 ± 0.5°, (〈C-C(F)-C)mean = 121.5 ± 0.2°. The angular ring deformation corresponds to additivity of the individual substituent effects with no appreciable consequence of substituent interaction within experimental error. The mean C-F bond length (rg) is 1.346 ± 0.005 Å. A mixture of two conformers with C2v and C2h symmetry is likely.

Original languageEnglish
Pages (from-to)5843-5846
Number of pages4
JournalJournal of physical chemistry
Volume96
Issue number14
DOIs
Publication statusPublished - Jan 1 1992

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ASJC Scopus subject areas

  • Engineering(all)
  • Physical and Theoretical Chemistry

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