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Updated: Jun 1, 2026
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
N'-(Butan-2-yl-idene)furan-2-carbohydrazide
Summary
A novel Schiff base compound was synthesized from butan-2-one and furan-2-carbohydrazide. Crystal analysis revealed a planar furan and hydrazide core with a slightly twisted butanyl-idene group, forming dimers via hydrogen bonds.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Schiff bases are versatile compounds with diverse applications.
- Furan derivatives and hydrazides are key building blocks in organic synthesis.
- Understanding molecular structure and intermolecular interactions is crucial for material design.
Purpose of the Study:
- To synthesize and characterize a novel Schiff base compound.
- To investigate the crystal structure and intermolecular interactions of the synthesized compound.
- To explore the structural features influencing the compound's properties.
Main Methods:
- Condensation reaction between butan-2-one and furan-2-carbohydrazide.
- Single-crystal X-ray diffraction analysis to determine molecular and crystal structure.
- Analysis of bond lengths, bond angles, and dihedral angles.
- Identification of intermolecular interactions, specifically hydrogen bonding.
Main Results:
- The Schiff base compound C(9)H(12)N(2)O(2) was successfully synthesized.
- X-ray crystallography confirmed the molecular structure, showing a planar furan and hydrazide moiety.
- A slight twist (dihedral angle of 5.2°) was observed in the butanyl-idene group relative to the planar core.
- Intermolecular N-H⋯O hydrogen bonds were identified, leading to the formation of R(2)(2)(8) dimers.
Conclusions:
- The synthesis yielded the target Schiff base with a defined molecular architecture.
- The crystal structure highlights the interplay between planarity and torsion within the molecule.
- Hydrogen bonding plays a significant role in the self-assembly of these molecules into dimers.
- This study provides foundational structural data for Schiff base compounds with furan moieties.
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