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Hydrogen bonding in 2,2,2-trifluoroethanol.

Soon Ng1, Yaoming Xie2, Henry F Schaefer2

  • 1Department of Chemistry, University of Malaya, 50603, Kuala Lumpur, Malaysia. ngsoon@um.edu.my.

Journal of Molecular Modeling
|September 14, 2024
PubMed
Summary

2,2,2-Trifluoroethanol (TFE) forms stable hydrogen-bonded trimers that mimic liquid crystal structures. This self-assembly may explain TFE's membrane-mimetic solvent properties.

Keywords:
2,2,2-TrifluoroethanolDFT computationsHydrogen bondingTrimers

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Area of Science:

  • Physical Chemistry
  • Computational Chemistry
  • Supramolecular Chemistry

Background:

  • 2,2,2-Trifluoroethanol (TFE) is recognized as a membrane-mimetic solvent.
  • Spectroscopic data (IR, NMR) indicate extensive hydrogen bonding in TFE, but lack detailed structural information.

Purpose of the Study:

  • To elucidate the structural features of hydrogen bonding in 2,2,2-Trifluoroethanol (TFE).
  • To investigate the self-assembly of TFE monomers into stable clusters.

Main Methods:

  • Density Functional Theory (DFT) computations using the ωB97X-D hybrid functional.
  • A triple-ζ quality basis set (6-311++G**) including polarization and diffuse functions was employed.
  • Analysis of hydrogen-bonded dimers and trimers, including bond lengths, dihedral angles, and dissociation energies.

Main Results:

  • DFT calculations predict the formation of stable hydrogen-bonded dimers and trimers of TFE.
  • Specific trimer structures were identified, including cyclic arrangements with free CF3CH2 side chains.
  • High dissociation energies confirm the stability of the trimer complexes.
  • Trimer structures exhibit similarities to liquid crystal molecules.

Conclusions:

  • The self-assembly of TFE into stable, liquid-crystal-like trimers is computationally demonstrated.
  • These structural features provide a potential explanation for TFE's membrane-mimetic solvent behavior.
  • The noncovalent interactions driving this self-assembly operate on a short timescale.