Molecular structure of ethynylbenzene from electron diffraction and ab initio molecular orbital calculations

György Schultz, Tamás Nagy, Gustavo Portalone, Fabio Ramondo, I. Hargittai, Aldo Domenicano

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The molecular structure and benzene ring distortions of ethynylbenzene have been investigated by gas-phase electron diffraction and ab initio MO calculations at the HF/6-31G* and 6-3G** levels. Least-squares refinement of a model with C2v, symmetry, with constraints from the MO calculations, yielded the following important bond distances and angles:rg(Ci-Co)=1.407±0.003 Å, rg(Co-Cm)=1.397±0.003 Å, rg(Cm-Cp)=1.400±0.003 Å, rg(Cri-CCH)=1.436 ±0.004 Å, rg(C=C)=1.205±0.005 Å, ∠Co-Ci-Co=119.8±0.4°. The deformation of the benzene ring of ethynylbenzene given by the MO calculations, including o-Ci-Co=119.4°, is insensitive to the basis set used and agrees with that obtained by low-temperature X-ray crystallography for the phenylethynyl fragment, C6H5-C≡C-, in two different crystal environments. The partial substitution structure of ethynylbenzene from microwave spectroscopy is shown to be inaccurate in the ipso region of the benzene ring.

Original languageEnglish
Pages (from-to)183-190
Number of pages8
JournalStructural Chemistry
Volume4
Issue number3
DOIs
Publication statusPublished - Jun 1993

Fingerprint

Orbital calculations
Molecular orbitals
Benzene
Molecular Structure
Electron diffraction
Molecular structure
molecular orbitals
molecular structure
electron diffraction
benzene
Electrons
rings
Microwave spectroscopy
X ray crystallography
X Ray Crystallography
Microwaves
Least-Squares Analysis
crystallography
Spectrum Analysis
Substitution reactions

Keywords

  • benzene ring deformation
  • ethynylbenzene
  • gas-phase electron diffraction
  • Substituted benzenes

ASJC Scopus subject areas

  • Chemistry(all)
  • Structural Biology

Cite this

Molecular structure of ethynylbenzene from electron diffraction and ab initio molecular orbital calculations. / Schultz, György; Nagy, Tamás; Portalone, Gustavo; Ramondo, Fabio; Hargittai, I.; Domenicano, Aldo.

In: Structural Chemistry, Vol. 4, No. 3, 06.1993, p. 183-190.

Research output: Contribution to journalArticle

Schultz, György ; Nagy, Tamás ; Portalone, Gustavo ; Ramondo, Fabio ; Hargittai, I. ; Domenicano, Aldo. / Molecular structure of ethynylbenzene from electron diffraction and ab initio molecular orbital calculations. In: Structural Chemistry. 1993 ; Vol. 4, No. 3. pp. 183-190.
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abstract = "The molecular structure and benzene ring distortions of ethynylbenzene have been investigated by gas-phase electron diffraction and ab initio MO calculations at the HF/6-31G* and 6-3G** levels. Least-squares refinement of a model with C2v, symmetry, with constraints from the MO calculations, yielded the following important bond distances and angles:rg(Ci-Co)=1.407±0.003 {\AA}, rg(Co-Cm)=1.397±0.003 {\AA}, rg(Cm-Cp)=1.400±0.003 {\AA}, rg(Cri-CCH)=1.436 ±0.004 {\AA}, rg(C=C)=1.205±0.005 {\AA}, ∠Co-Ci-Co=119.8±0.4°. The deformation of the benzene ring of ethynylbenzene given by the MO calculations, including o-Ci-Co=119.4°, is insensitive to the basis set used and agrees with that obtained by low-temperature X-ray crystallography for the phenylethynyl fragment, C6H5-C≡C-, in two different crystal environments. The partial substitution structure of ethynylbenzene from microwave spectroscopy is shown to be inaccurate in the ipso region of the benzene ring.",
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