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Updated: Jun 24, 2025
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
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2-(10-Bromo-anthracen-9-yl)-N-phenyl-aniline
Dhandayutham Saravanan1, C Ponraj1, Themmila Khamrang2
1Department of Chemistry, National College, Thiruchirappalli, Tamil Nadu, India.
Iucrdata
|June 7, 2024
Summary
This study details the molecular structure of a novel brominated organic compound. Analysis reveals specific dihedral angles between its aromatic rings and hindered hydrogen bonding, suggesting unique intermolecular interactions.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties.
- Aromatic systems and their spatial orientation significantly influence molecular packing and intermolecular forces.
- Brominated organic compounds can exhibit unique electronic and structural characteristics.
Purpose of the Study:
- To elucidate the precise molecular geometry of the title compound, C26H18BrN.
- To investigate the nature of intermolecular interactions within the crystal structure.
- To correlate structural features with potential chemical and physical properties.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of dihedral angles between aromatic systems was performed.
- Intermolecular interactions, including hydrogen bonding and C-H···π interactions, were identified and analyzed.
Main Results:
- The central benzene ring exhibited significant dihedral angles of 87.49(13)° and 62.01(17)° with the adjacent anthracene and pendant benzene rings, respectively.
- The N-H group was sterically hindered, preventing intramolecular hydrogen bonding.
- Weak C-H···π interactions were observed in the extended crystal lattice.
Conclusions:
- The determined structure of C26H18BrN reveals a non-planar conformation due to restricted rotation around single bonds.
- Steric hindrance around the N-H group limits hydrogen bond formation, directing intermolecular interactions towards weaker forces like C-H···π.
- These structural insights are vital for designing related organic materials with tailored properties.
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