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Updated: Jun 5, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
2,2'-(Biphenyl-2,2'-diyldi-oxy)diaceto-hydrazide
This study details the crystal structure of C(16)H(18)N(4)O(4), highlighting significant intermolecular hydrogen bonds. These interactions, involving amines and carbonyl groups, stabilize the molecular arrangement without π-π stacking.
Area of Science:
- Crystallography
- Molecular Structure
- Supramolecular Chemistry
Background:
- Understanding the three-dimensional arrangement of molecules is crucial in chemistry.
- Hydrogen bonding plays a significant role in stabilizing crystal structures.
- The specific compound C(16)H(18)N(4)O(4) has not been previously characterized in detail.
Purpose of the Study:
- To elucidate the detailed crystal structure of the title compound, C(16)H(18)N(4)O(4).
- To identify and analyze the types and extent of intermolecular and intramolecular interactions present.
- To characterize the dihedral angle between the two benzene rings within the molecule.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of hydrogen bonding networks, including motif analysis (R(2)(2)(10) and R(2)(2)(6)).
- Measurement of the dihedral angle between the two benzene rings.
Main Results:
- The dihedral angle between the two benzene rings was determined to be 56.76(5)°.
- Extensive intermolecular hydrogen bonds were observed between carbonyl oxygen atoms and primary amines.
- Further intermolecular hydrogen bonds were found between primary and secondary amines of the hydrazide moiety.
- Intramolecular and non-classical hydrogen bonds (N-H⋯O and C-H⋯O) contribute to structural stabilization.
- No π-π interactions were detected in the crystal structure.
Conclusions:
- The crystal structure of C(16)H(18)N(4)O(4) is characterized by a specific dihedral angle between its benzene rings.
- The molecular architecture is significantly stabilized by a complex network of intermolecular and intramolecular hydrogen bonds.
- The absence of π-π interactions provides insight into the packing forces governing this specific crystal structure.
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