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Benzaldehyde 2,4-dinitrophenylhydrazone.

Shang Shan1, Duan-Jun Xu, Chen-Hsiung Hung

  • 1College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, Zhejiang, People's Republic of China.

Acta Crystallographica. Section C, Crystal Structure Communications
|April 25, 2003
PubMed
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Crystals of a benzaldehyde derivative were analyzed, revealing an E configuration and significant differences in aromatic carbon-carbon bond lengths. These structural findings suggest potential pi-pi stacking interactions within the crystal lattice.

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure

Background:

  • Benzaldehyde and 2,4-dinitrophenylhydrazine are common organic compounds.
  • Condensation reactions are fundamental in organic synthesis.
  • Understanding molecular geometry and intermolecular forces is crucial in chemistry.

Purpose of the Study:

  • To characterize the crystal structure of the condensation product of benzaldehyde and 2,4-dinitrophenylhydrazine.
  • To investigate the molecular geometry and electronic properties of the title compound.
  • To explore potential intermolecular interactions, such as pi-pi stacking, in the solid state.

Main Methods:

  • Single crystal X-ray diffraction was used to determine the molecular structure.
  • Analysis of bond lengths and angles within the dinitrophenyl moiety.

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  • Examination of crystal packing to identify intermolecular interactions.

    • Main Results:

    • The compound C(13)H(10)N(4)O(4) was successfully synthesized and crystallized.
    • The molecule adopts an approximately planar E configuration.
    • A significant difference in aromatic C-C bond lengths was observed in the dinitrophenyl group, with bonds near the imino group being longer.
    • Evidence suggests the presence of pi-pi stacking in the crystal structure.

    Conclusions:

    • The structural analysis provides insights into the electronic effects influencing bond lengths in aromatic systems.
    • The observed bond length variations are likely due to orbital overlap between the imino nitrogen and the aromatic ring.
    • The study highlights the importance of crystal packing and pi-pi interactions in stabilizing the solid-state structure.