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Updated: Jun 5, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(E)-4-(5-Hydr-oxy-2-methyl-benzyl-idene-amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
1Department of Chemistry, Lishui University, Lishui 323000, People's Republic of China.
This study details a new Schiff base compound, C(19)H(19)N(3)O(2), synthesized from 4-amino-anti-pyrine and 5-hydroxy-2-methyl-benzaldehyde. Structural analysis reveals a trans configuration and specific hydrogen bonding patterns influencing crystal packing.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Schiff bases are versatile organic compounds with diverse applications.
- The synthesis and structural characterization of novel Schiff bases are crucial for materials science and medicinal chemistry.
- 4-amino-anti-pyrine and 5-hydroxy-2-methyl-benzaldehyde are key precursors for Schiff base synthesis.
Purpose of the Study:
- To synthesize and characterize a novel Schiff base compound.
- To elucidate the molecular structure and crystal packing of the title compound.
- To investigate the intermolecular interactions, including hydrogen bonding, within the crystal lattice.
Main Methods:
- Chemical synthesis of the Schiff base.
- Single-crystal X-ray diffraction for structural determination.
- Analysis of molecular geometry and hydrogen bonding interactions.
Main Results:
- The title compound, C(19)H(19)N(3)O(2), was successfully synthesized.
- X-ray crystallographic analysis confirmed the molecular structure, revealing a trans configuration around the C=N bond.
- Intra-molecular O-H⋯N and weak inter-molecular C-H⋯O hydrogen bonds were identified, leading to chain formation along the b axis.
Conclusions:
- The synthesized Schiff base exhibits a defined molecular structure with specific hydrogen bonding motifs.
- The identified hydrogen bonding network dictates the crystal packing, forming a chain structure.
- This structural insight contributes to the understanding of Schiff base chemistry and crystal engineering.
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