Related Experiment Video
Updated: Jun 5, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
2-Hydr-oxy-N'-(2-methoxy-naphthyl-idene)benzohydrazide
1Department of Chemistry, Shangqiu Normal University, Shangqiu 476000, People's Republic of China.
This study details the crystal structure of a Schiff base compound, C(19)H(16)N(2)O(3). The compound exhibits trans configurations and stabilizes through intra- and inter-molecular hydrogen bonds, forming one-dimensional chains.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Schiff base compounds are versatile organic molecules with diverse applications.
- Understanding the solid-state structure of Schiff bases is crucial for predicting their properties and designing new materials.
- The synthesis and characterization of novel Schiff base derivatives contribute to the field of coordination chemistry.
Purpose of the Study:
- To determine the crystal structure of the Schiff base compound C(19)H(16)N(2)O(3).
- To analyze the molecular conformation, including the configuration around the methylidene group and dihedral angles between aromatic systems.
- To investigate the role of intra- and inter-molecular hydrogen bonding in stabilizing the crystal structure.
Main Methods:
- Single-crystal X-ray diffraction was employed to elucidate the crystal structure.
- The crystallographic data was analyzed to determine molecular geometry and packing arrangements.
- Hydrogen bonding interactions were identified and characterized.
Main Results:
- The Schiff base compound C(19)H(16)N(2)O(3) crystallizes with two independent molecules in the asymmetric unit.
- Each molecule adopts a trans configuration about the methylidene group, with dihedral angles of 65.0(2)° and 55.8(2)° between the naphthyl and benzene rings.
- Intra-molecular hydrogen bonds (N-H⋯O and O-H⋯O) stabilize individual molecules, while inter-molecular hydrogen bonds (O-H⋯N and O-H⋯O) link molecules into 1D chains along the c-axis.
Conclusions:
- The crystal structure of the Schiff base C(19)H(16)N(2)O(3) has been successfully determined.
- The study highlights the importance of hydrogen bonding in directing the self-assembly of Schiff base molecules in the solid state.
- The findings provide valuable insights into the structure-property relationships of this class of compounds.
Related Concept Videos
Hydrolysis of Chlorobenzene to Phenol: Dow Process
Diazonium Group Substitution: –OH and –H
Nucleophilic Aromatic Substitution: Elimination–Addition
Formation of Halohydrin from Alkenes
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

