Hydrogen bonding in 2-trifluoromethylresorcinol and 2,6-bis(trifluoromethyl)phenol and its geometrical consequences

Attila Kovács, I. Hargittai

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The potential energy hypersurface of 2-trifluoromethylresorcinol and 2,6-bis(trifluoromethyl)phenol has been studied by quantum chemical computations at the HF/6-31G** and MP2/6-31G** levels of theory. The global minimum is stabilized by two hydrogen bonds in 2-trifluoromethylresorcinol and by one in 2,6-bis(trifluoromethyl)phenol. The OH⋯F hydrogen bonding is accompanied by characteristic changes of the molecular geometry, compared with the 'parent' compounds, phenol, trifluoromethylbenzene, resorcinol and meta-bis(trifluoromethyl)benzene. These changes include: a lengthening of the C-F bond involved in the interaction (0.013-0.020 Å), a shortening of the C-O bond (0.007 Å), and a lengthening of the ring C-C bond between the interacting substituents (0.009-0.016 Å). The length of the O-H bonds appears unaffected in these OH⋯F interactions, at variance with the usual observation for OH⋯O and OH⋯N hydrogen bonding.

Original languageEnglish
Pages (from-to)229-238
Number of pages10
JournalJournal of Molecular Structure: THEOCHEM
Volume455
Issue number2-3
Publication statusPublished - Dec 18 1998

Fingerprint

Hydrogen Bonding
Phenol
phenols
Phenols
Hydrogen bonds
hydrogen
Potential energy
Benzene
Hydrogen
potential energy
benzene
Observation
interactions
hydrogen bonds
Geometry
rings
geometry

Keywords

  • 2,6-Bis(trifluoromethyl)phenol
  • 2-Trifluoromethylresorcinol
  • Ab initio calculations
  • AIM analysis
  • Resonance-assisted hydrogen bonding

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

Hydrogen bonding in 2-trifluoromethylresorcinol and 2,6-bis(trifluoromethyl)phenol and its geometrical consequences. / Kovács, Attila; Hargittai, I.

In: Journal of Molecular Structure: THEOCHEM, Vol. 455, No. 2-3, 18.12.1998, p. 229-238.

Research output: Contribution to journalArticle

@article{0989df85fac544e28f7362581838a5e7,
title = "Hydrogen bonding in 2-trifluoromethylresorcinol and 2,6-bis(trifluoromethyl)phenol and its geometrical consequences",
abstract = "The potential energy hypersurface of 2-trifluoromethylresorcinol and 2,6-bis(trifluoromethyl)phenol has been studied by quantum chemical computations at the HF/6-31G** and MP2/6-31G** levels of theory. The global minimum is stabilized by two hydrogen bonds in 2-trifluoromethylresorcinol and by one in 2,6-bis(trifluoromethyl)phenol. The OH⋯F hydrogen bonding is accompanied by characteristic changes of the molecular geometry, compared with the 'parent' compounds, phenol, trifluoromethylbenzene, resorcinol and meta-bis(trifluoromethyl)benzene. These changes include: a lengthening of the C-F bond involved in the interaction (0.013-0.020 {\AA}), a shortening of the C-O bond (0.007 {\AA}), and a lengthening of the ring C-C bond between the interacting substituents (0.009-0.016 {\AA}). The length of the O-H bonds appears unaffected in these OH⋯F interactions, at variance with the usual observation for OH⋯O and OH⋯N hydrogen bonding.",
keywords = "2,6-Bis(trifluoromethyl)phenol, 2-Trifluoromethylresorcinol, Ab initio calculations, AIM analysis, Resonance-assisted hydrogen bonding",
author = "Attila Kov{\'a}cs and I. Hargittai",
year = "1998",
month = "12",
day = "18",
language = "English",
volume = "455",
pages = "229--238",
journal = "Computational and Theoretical Chemistry",
issn = "2210-271X",
publisher = "Elsevier BV",
number = "2-3",

}

TY - JOUR

T1 - Hydrogen bonding in 2-trifluoromethylresorcinol and 2,6-bis(trifluoromethyl)phenol and its geometrical consequences

AU - Kovács, Attila

AU - Hargittai, I.

PY - 1998/12/18

Y1 - 1998/12/18

N2 - The potential energy hypersurface of 2-trifluoromethylresorcinol and 2,6-bis(trifluoromethyl)phenol has been studied by quantum chemical computations at the HF/6-31G** and MP2/6-31G** levels of theory. The global minimum is stabilized by two hydrogen bonds in 2-trifluoromethylresorcinol and by one in 2,6-bis(trifluoromethyl)phenol. The OH⋯F hydrogen bonding is accompanied by characteristic changes of the molecular geometry, compared with the 'parent' compounds, phenol, trifluoromethylbenzene, resorcinol and meta-bis(trifluoromethyl)benzene. These changes include: a lengthening of the C-F bond involved in the interaction (0.013-0.020 Å), a shortening of the C-O bond (0.007 Å), and a lengthening of the ring C-C bond between the interacting substituents (0.009-0.016 Å). The length of the O-H bonds appears unaffected in these OH⋯F interactions, at variance with the usual observation for OH⋯O and OH⋯N hydrogen bonding.

AB - The potential energy hypersurface of 2-trifluoromethylresorcinol and 2,6-bis(trifluoromethyl)phenol has been studied by quantum chemical computations at the HF/6-31G** and MP2/6-31G** levels of theory. The global minimum is stabilized by two hydrogen bonds in 2-trifluoromethylresorcinol and by one in 2,6-bis(trifluoromethyl)phenol. The OH⋯F hydrogen bonding is accompanied by characteristic changes of the molecular geometry, compared with the 'parent' compounds, phenol, trifluoromethylbenzene, resorcinol and meta-bis(trifluoromethyl)benzene. These changes include: a lengthening of the C-F bond involved in the interaction (0.013-0.020 Å), a shortening of the C-O bond (0.007 Å), and a lengthening of the ring C-C bond between the interacting substituents (0.009-0.016 Å). The length of the O-H bonds appears unaffected in these OH⋯F interactions, at variance with the usual observation for OH⋯O and OH⋯N hydrogen bonding.

KW - 2,6-Bis(trifluoromethyl)phenol

KW - 2-Trifluoromethylresorcinol

KW - Ab initio calculations

KW - AIM analysis

KW - Resonance-assisted hydrogen bonding

UR - http://www.scopus.com/inward/record.url?scp=0346548741&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0346548741&partnerID=8YFLogxK

M3 - Article

VL - 455

SP - 229

EP - 238

JO - Computational and Theoretical Chemistry

JF - Computational and Theoretical Chemistry

SN - 2210-271X

IS - 2-3

ER -