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But-2-enal 2,4-dinitro-phenyl-hydrazone.

Zhi-Gang Yin1, Heng-Yu Qian, Yu-Zhen Chen

  • 1Key Laboratory of Surface and Interface Science of Henan, School of Materials and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China.

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

This study details the molecular structure of C(10)H(10)N(4)O(4), revealing specific bond angles and the influence of intramolecular hydrogen bonding on nitro group orientation. These findings offer insights into crystal packing and molecular interactions.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure Analysis

Background:

  • Understanding molecular geometry is crucial for predicting chemical properties and reactivity.
  • Nitro-substituted aromatic compounds exhibit diverse conformational behaviors influenced by steric and electronic factors.

Purpose of the Study:

  • To elucidate the detailed three-dimensional molecular structure of the title compound, C(10)H(10)N(4)O(4).
  • To investigate the conformational preferences of the but-2-enal chain and nitro groups relative to the benzene ring.
  • To identify and analyze intramolecular and intermolecular interactions, such as hydrogen bonding, that influence molecular conformation.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the precise atomic coordinates and bond parameters.
  • Analysis of dihedral angles and deviations from planarity provided insights into the molecular geometry.
  • Identification of hydrogen bonds and other non-covalent interactions was performed.

Main Results:

  • The but-2-enal chain in C(10)H(10)N(4)O(4) was found to be nearly planar, with minimal deviation from its mean plane.
  • One nitro group exhibited significant twisting relative to the benzene ring (5.7°), while the other remained nearly coplanar (0.7°).
  • An intramolecular N-H⋯O hydrogen bond was observed between the NH group and the oxygen atom of the less twisted nitro group, stabilizing this conformation.
  • A pseudo inversion dimer was formed through a weak intermolecular interaction involving the NH group and a symmetry-related molecule.

Conclusions:

  • The molecular structure of C(10)H(10)N(4)O(4) is characterized by specific conformational preferences of its substituents.
  • Intramolecular hydrogen bonding plays a significant role in dictating the orientation of the nitro groups.
  • The formation of pseudo inversion dimers through intermolecular interactions influences the crystal packing.