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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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For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

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9,10-Diiodo-phenanthrene.

Ruri Yokota1, Chitoshi Kitamura, Takeshi Kawase

  • 1Department of Materials Science and Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280, Japan.

Acta Crystallographica. Section E, Structure Reports Online
|March 12, 2013
PubMed
Summary

This study reveals the planar structure of C14H8I2, showcasing its unique π-π stacking interactions in crystal formation. These findings offer insights into molecular arrangement and intermolecular forces.

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Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Organic chemistry

Background:

  • Understanding molecular structure and intermolecular forces is crucial in materials science.
  • Phenanthrene derivatives are important in various chemical applications.
  • Detailed crystallographic studies provide fundamental insights into chemical bonding and packing.

Purpose of the Study:

  • To determine the precise crystal structure of the title compound, C14H8I2.
  • To analyze the planarity of the molecule and the position of iodine atoms.
  • To investigate the intermolecular interactions, specifically π-π stacking, within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to elucidate the three-dimensional structure.
  • Crystallographic symmetry operations were used to generate the complete molecular structure.
  • Analysis of atomic coordinates and bond distances provided information on planarity and deviations.

Main Results:

  • The C14H8I2 molecule adopts a planar conformation, with minimal deviation from the mean plane.
  • Iodine atoms are only slightly displaced from the phenanthrene ring system's plane.
  • Molecules exhibit face-to-face, slipped anti-parallel π-π stacking along the c-axis with an inter-planar distance of 3.499 Å.

Conclusions:

  • The title compound C14H8I2 possesses a highly planar molecular geometry.
  • The observed π-π stacking interactions are significant for the crystal packing and material properties.
  • This structural characterization contributes to the understanding of halogenated polycyclic aromatic hydrocarbons.