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Updated: Jun 1, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
1,3-Diphenyl-propan-2-one (2,4-dinitro-phen-yl)hydrazone.
This study details the crystal structure of a novel organic compound, C(21)H(18)N(4)O(4). Key findings include an intramolecular hydrogen bond and a three-dimensional network formed by weak intermolecular interactions.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding molecular interactions is crucial in materials science.
- Crystal engineering relies on predicting and controlling intermolecular forces.
- The study of novel organic compounds provides insights into chemical bonding.
Purpose of the Study:
- To elucidate the crystal structure of the compound C(21)H(18)N(4)O(4).
- To identify and analyze intramolecular and intermolecular interactions within the crystal lattice.
- To characterize the spatial arrangement of the molecule in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided structural details.
- Intermolecular interaction analysis (e.g., hydrogen bonds, C-H interactions) was performed.
Main Results:
- An intramolecular N-H⋯O hydrogen bond was identified between the amino group and a nitro group.
- The central benzene ring exhibited significant dihedral angles (79.98(7)° and 82.88(7)°) with the two phenyl rings.
- A three-dimensional network was formed through weak C-H⋯N, C-H⋯O, and C-H⋯π interactions.
Conclusions:
- The compound C(21)H(18)N(4)O(4) exhibits specific intramolecular hydrogen bonding.
- The non-planar conformation of the molecule influences crystal packing.
- Weak interactions play a significant role in constructing the observed 3D supramolecular architecture.
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The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
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