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Reactions at the Benzylic Position: Halogenation01:11

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Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
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3-(2-Hy-droxy-eth-yl)-1-(4-nitro-phen-yl)-1H-benzo[d]imidazol-3-ium bromide.

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Summary

This study details the crystal structure of a novel salt, revealing specific molecular angles and hydrogen bonding interactions. These interactions form a unique two-dimensional supramolecular network in the crystal lattice.

Keywords:
benzoimidazolium saltcrystal structuretetra­mer

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Understanding the three-dimensional arrangement of molecules in crystalline solids is crucial for predicting material properties.
  • Hydrogen bonding plays a significant role in the self-assembly of molecules and the formation of extended networks.

Purpose of the Study:

  • To elucidate the crystal structure of the title salt, C15H14N3O3+·Br−.
  • To analyze the conformational details, including dihedral and torsion angles, of the cation.
  • To investigate the intermolecular interactions, particularly hydrogen bonding, that govern the crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, dihedral angles, and torsion angles.
  • Identification and characterization of hydrogen bonding networks (O-H⋯Br, C-H⋯Br, C-H⋯O).

Main Results:

  • The cation exhibits a dihedral angle of 24.26(6)° between the imidazole and 4-nitro-phenyl rings.
  • The hydroxy-ethyl substituent shows an N-C-C-O torsion angle of 60.15(17)°.
  • Bromide ions act as hydrogen bond acceptors from both the hydroxyl group and the imidazolium moiety.
  • C-H⋯O hydrogen bonds link the phenyl and hydroxyl groups, forming a 2D supramolecular network in the bc plane.

Conclusions:

  • The crystal structure reveals specific conformational preferences of the organic cation.
  • The identified hydrogen bonding patterns dictate the formation of a robust two-dimensional supramolecular architecture.
  • This structural insight contributes to the understanding of crystal engineering principles for organic salts.