Geometrical consequences of resonance-assisted hydrogen bonding in 2-nitrovinyl alcohol and indication of a slight attractive O⋯H interaction in 2-nitroethanol. An ab initio molecular orbital investigation

Tereza Varnali, I. Hargittai

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Ab initio molecular orbital calculations on 2-nitrovinyl alcohol and 2-nitroethanol and their parent structures have been performed with a 6-31G** basis set, including electron correlation using second-order Møller-Plesset perturbation theory. There is resonance-assisted hydrogen bonding in 2-vinyl alcohol, as witnessed by a 1.75 Å long O⋯H interaction and considerable bond length changes in the rest of the molecule, as compared with nitroethylene and vinyl alcohol. Slight bond length changes in 2-nitroethanol point to some attractive O⋯H interaction even in 2-nitroethanol.

Original languageEnglish
Pages (from-to)315-319
Number of pages5
JournalJournal of Molecular Structure: THEOCHEM
Volume388
Issue number1-3
Publication statusPublished - Dec 11 1996

Fingerprint

Molecular orbitals
Hydrogen Bonding
molecular orbitals
Hydrogen bonds
indication
alcohols
Alcohols
Bond length
hydrogen
Electron correlations
Orbital calculations
interactions
perturbation theory
Electrons
Molecules
molecules
electrons

Keywords

  • Ab initio calculation
  • Hydrogen bonding
  • Møller-Plesset perturbation theory
  • Nitrated alcohol
  • Resonance-assisted hydrogen bonding

ASJC Scopus subject areas

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

Cite this

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abstract = "Ab initio molecular orbital calculations on 2-nitrovinyl alcohol and 2-nitroethanol and their parent structures have been performed with a 6-31G** basis set, including electron correlation using second-order M{\o}ller-Plesset perturbation theory. There is resonance-assisted hydrogen bonding in 2-vinyl alcohol, as witnessed by a 1.75 {\AA} long O⋯H interaction and considerable bond length changes in the rest of the molecule, as compared with nitroethylene and vinyl alcohol. Slight bond length changes in 2-nitroethanol point to some attractive O⋯H interaction even in 2-nitroethanol.",
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AB - Ab initio molecular orbital calculations on 2-nitrovinyl alcohol and 2-nitroethanol and their parent structures have been performed with a 6-31G** basis set, including electron correlation using second-order Møller-Plesset perturbation theory. There is resonance-assisted hydrogen bonding in 2-vinyl alcohol, as witnessed by a 1.75 Å long O⋯H interaction and considerable bond length changes in the rest of the molecule, as compared with nitroethylene and vinyl alcohol. Slight bond length changes in 2-nitroethanol point to some attractive O⋯H interaction even in 2-nitroethanol.

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