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4,7-Dimethoxybenzo[c]furan

V M Lynch1, R A Fairhurst, P Magnus

  • 1Department of Chemistry & Biochemistry, University of Texas at Austin 78712, USA.

Acta Crystallographica. Section C, Crystal Structure Communications
|April 15, 1995
PubMed
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This study reveals the benzo[c]furan moiety in C10H10O3 is non-aromatic, featuring alternating bond lengths characteristic of diene systems. Close intermolecular contacts likely stabilize this unique molecular structure in the solid state.

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Geometry

Background:

  • Benzo[c]furan derivatives are important in medicinal chemistry.
  • Understanding the electronic and structural properties of heterocyclic compounds is crucial.

Purpose of the Study:

  • To elucidate the molecular geometry and electronic structure of the title compound, C10H10O3.
  • To determine if the benzo[c]furan moiety exhibits aromaticity.

Main Methods:

  • Single-crystal X-ray diffraction analysis was performed.
  • Bond lengths and deviations from planarity were analyzed.

Main Results:

  • The compound C10H10O3 is nearly planar, with a maximum deviation of 0.140(2) Å.

Related Experiment Videos

  • The benzo[c]furan ring system displays alternating long (1.437(2) Å) and short (1.354(2) Å) C-C bonds, indicative of a non-aromatic diene system.
  • Close intermolecular C-H ... O contacts were observed.

    • Conclusions:

    • The benzo[c]furan moiety in C10H10O3 is confirmed to be non-aromatic.
    • The observed geometry and bonding suggest two non-interacting diene systems.
    • Intermolecular interactions play a role in stabilizing the crystal structure.