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Updated: Jun 5, 2026
06:46
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(E)-2-(Benzyl-imino-meth-yl)-4,6-dibromo-phenol
1College of Chemistry and Life Sciences, Maoming University, Guandu Second Road 139, Maoming 525000, People's Republic of China.
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
Researchers synthesized a novel compound, C(14)H(11)Br(2)NO, using benzylamine and a dibromohydroxybenzaldehyde derivative. Crystal structure analysis revealed stabilization through aromatic π-π stacking and hydrogen bonding interactions.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- The synthesis of novel organic compounds is crucial for developing new materials and pharmaceuticals.
- Understanding intermolecular forces, such as π-π stacking and hydrogen bonding, is key to predicting and controlling crystal structures.
- Benzaldehyde derivatives are versatile building blocks in organic synthesis.
Purpose of the Study:
- To synthesize and characterize a new organic compound with the molecular formula C(14)H(11)Br(2)NO.
- To elucidate the crystal structure of the synthesized compound.
- To investigate the nature of intermolecular interactions stabilizing the crystal lattice.
Main Methods:
- Condensation reaction between benzylamine and 3,5-dibromo-2-hydroxybenzaldehyde.
- Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.
- Analysis of non-covalent interactions, including π-π stacking and hydrogen bonding.
Main Results:
- Successful synthesis of the target compound C(14)H(11)Br(2)NO.
- Determination of the crystal structure, revealing a unique arrangement of molecules in the solid state.
- Identification of stabilizing interactions: aromatic π-π stacking between phenol rings (centroid-centroid distance = 3.530(5) Å), intermolecular C-H⋯π interactions, and intramolecular O-H⋯N hydrogen bonds.
Conclusions:
- The synthesized compound exhibits a crystal structure stabilized by a combination of π-π stacking and hydrogen bonding.
- The findings provide insights into the structure-property relationships of halogenated organic molecules.
- This study contributes to the understanding of supramolecular assembly in organic crystals.
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