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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
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Introduction
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Decachloro-hexa-1,5-diene.

Dieter Schollmeyer1, Heiner Detert

  • 1University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|June 22, 2012
PubMed
Summary
This summary is machine-generated.

Hexachloroethane (C6Cl10) crystallizes in a gauche conformation. Structural analysis reveals near-planar trichloro-vinyl groups and varying C-Cl bond lengths and angles, indicating unique molecular geometry.

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Area of Science:

  • Crystallography
  • Inorganic Chemistry
  • Molecular Structure

Background:

  • Understanding the solid-state structure of halogenated organic compounds is crucial for predicting their chemical behavior and physical properties.
  • Previous studies on similar compounds provide a basis for comparison of structural parameters.

Purpose of the Study:

  • To elucidate the crystal structure and molecular geometry of hexachloroethane (C6Cl10).
  • To analyze bond lengths, bond angles, and conformational preferences within the molecule.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the crystal structure.
  • Geometric parameters such as bond lengths, bond angles, and torsion angles were precisely measured.

Main Results:

  • Hexachloroethane (C6Cl10) crystallizes in a nearly C2-symmetrical gauche conformation.
  • Trichloro-vinyl groups exhibit near planarity with specific Cl-C-C-Cl torsion angles.
  • C-Cl bond lengths increase towards the interior of the molecule.
  • Terminal Cl-C-Cl bond angles are compressed.

Conclusions:

  • The observed gauche conformation and specific geometric distortions in hexachloroethane (C6Cl10) are key features of its solid-state structure.
  • These findings contribute to the understanding of structure-property relationships in highly chlorinated organic molecules.