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Related Experiment Video

Updated: Jun 1, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

Lophine (2,4,5-triphenyl-1H-imidazole).

Diana Yanover1, Menahem Kaftory

  • 1Schulich Faculty of Chemistry, Technion - Israel Institute of Technology, Haifa 32000, Israel.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

The crystal structure of the lophine compound C(21)H(16)N(2) was determined for the first time. Its phenyl rings are non-planar with the imidazole core, and no hydrogen bonds were observed in the crystal.

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Lophine (C(21)H(16)N(2)) has been known since 1877.
  • Crystal structures of 36 lophine derivatives are documented.
  • The crystal structure of the parent lophine compound remained undetermined until this study.

Purpose of the Study:

  • To determine the crystal structure of the parent lophine compound.
  • To analyze the molecular geometry and packing of lophine.
  • To compare the structural features of lophine with its known derivatives.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of dihedral angles between the imidazole core and phenyl rings.
  • Investigation of intermolecular interactions, including hydrogen bonding, within the crystal lattice.

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Published on: November 2, 2016

Main Results:

  • The crystal structure of lophine was successfully elucidated.
  • The three phenyl rings attached to the imidazole core are non-coplanar, exhibiting dihedral angles of 21.4°(3), 24.7°(3), and 39.0°(3) at the 2-, 4-, and 5-positions, respectively.
  • Lophine molecules are arranged in layers perpendicular to the b axis.
  • Despite the presence of potential hydrogen bond donors and acceptors, no intermolecular hydrogen bonds were detected in the crystal structure.

Conclusions:

  • This study provides the first determined crystal structure of the parent lophine compound.
  • The non-planar arrangement of the phenyl rings is a key structural feature.
  • The absence of hydrogen bonding in the crystal lattice distinguishes lophine from its derivatives.