Hydrogen-bonding interactions of the trifluoromethyl group: 2-Trifluoromethylvinyl alcohol

Attila Kovács, István Hargittai

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

As part of our investigation of intramolecular hydrogen bonding and its geometrical consequences, ab initio molecular orbital calculations on 2-trifluoromethylphenol and 2-trifluoromethylvinyl alcohol and their parent structures were performed at the MP2/6-31+G** level of theory. The intramolecular hydrogen bonding in 2-trifluoromethylvinyl alcohol appears stronger than that in 2-trifluoromethylphenol as witnessed by the shorter F ⋯ H interaction (1.96 Å) and the greater bond length changes in the rest of the molecule, as compared with the respective parent molecules. Beyond the geometrical characteristics, the energetics of hypothetical isodesmic reactions and the small shift of the O - H stretching frequency indicate that these C - F ⋯ H - O interactions are rather weak.

Original languageEnglish
Pages (from-to)645-652
Number of pages8
JournalInternational Journal of Quantum Chemistry
Volume62
Issue number6
DOIs
Publication statusPublished - Jan 1 1997

Keywords

  • 2-trifluoromethylphenol
  • 2-trifluoromethylvinyl alcohol
  • Isodesmic reactions
  • MP2/6-31+G** study
  • O - H stretching vibration
  • Resonance-assisted hydrogen bonding

ASJC Scopus subject areas

  • Atomic and Molecular Physics, and Optics
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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