Molecular structure and ring distortions of cyanobenzene: an electron diffraction study

Gustavo Portalone, Aldo Domenicano, György Schultz, István Hargittai

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28 Citations (Scopus)

Abstract

The molecular structure of cyanobenzene has been investigated by gas-phase electron diffraction. Least-squares refinement of a model with C2v symmetry leads to an accurate determination of the angular distortion of the ring at the place of substitution. The value of the internal angle at the ipso carbon, α = 121.9 ± 0.3°, is in excellent agreement with that obtained by microwave spectroscopy. The smaller value obtained by X-ray crystallography from several para-substituted cyanobenzenes, α = 121.1(2)°, probably reflects a change in the electronic properties of the cyano group, caused by strong intermolecular interactions in the solid state. Comparison of the experimental geometry of the ring in the free molecule with that obtained by ab initio MO calculations at the 6-31G and 6-31G** levels indicates that the calculations do not reproduce the angular distortion of the ipso region. Other important parameters from the present study are: 〈rg(CC)〉 = 1.400 ± 0.003 Å; rg(CCN) = 1.438 ± 0.005 Å; rg(CN) = 1.168 ± 0.003 Å.

Original languageEnglish
Pages (from-to)97-107
Number of pages11
JournalJournal of Molecular Structure
Volume160
Issue number1-2
DOIs
Publication statusPublished - Aug 1987

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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