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Related Experiment Videos

1,2-dinitroguanidine.

Alexander D Vasiliev1, Alexander M Astachov, Maxim S Molokeev

  • 1Institute of Physics, Krasnoyarsk 660036, Russia. adva@iph.krasn.ru

Acta Crystallographica. Section C, Crystal Structure Communications
|October 9, 2003
PubMed
Summary
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This study reveals the near-planar structure of CH(3)N(5)O(4), stabilized by intramolecular hydrogen bonds. Electron delocalization results in bond lengths intermediate between single and double bonds, indicating significant through-conjugation.

Area of Science:

  • Chemical Crystallography
  • Molecular Structure
  • Organic Chemistry

Background:

  • Understanding molecular conformation and electronic properties is crucial in chemistry.
  • Intramolecular hydrogen bonds play a significant role in stabilizing molecular structures.
  • Pi-electron delocalization influences bond characteristics and reactivity.

Purpose of the Study:

  • To elucidate the precise molecular structure of the title compound, CH(3)N(5)O(4).
  • To investigate the role of intramolecular hydrogen bonds in fixing the molecular conformation.
  • To analyze the electronic properties, specifically pi-electron delocalization and its effect on bond lengths.

Main Methods:

  • X-ray crystallography was employed to determine the three-dimensional structure.

Related Experiment Videos

  • Analysis of bond lengths and angles to assess electronic distribution.
  • Identification and analysis of intramolecular hydrogen bonding interactions.

    • Main Results:

    • The title compound, CH(3)N(5)O(4), exhibits an almost planar molecular geometry.
    • Two intramolecular N-H...O hydrogen bonds were identified, effectively locking the conformation.
    • Observed bond lengths (C-N, N-N, N-O) are intermediate between single and double bond values, signifying through-conjugation.

    Conclusions:

    • The molecular structure of CH(3)N(5)O(4) is significantly influenced by intramolecular hydrogen bonding.
    • Extensive pi-electron delocalization across the molecule leads to partial double bond character in various bonds.
    • The findings provide insights into the electronic structure and bonding in related nitrogen-rich compounds.