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Updated: Jun 1, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Methyl 2-[2-(2,6-dichloro-anilino)-phenyl]-acetate
Summary
This study details the crystal structure of a novel organic compound, C(15)H(13)Cl(2)NO(2). Key findings include a specific dihedral angle between aromatic rings and a notable C-Cl⋯π interaction in its solid-state conformation.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the solid-state behavior of organic molecules is crucial for predicting their physical and chemical properties.
- Intermolecular interactions, such as hydrogen bonding and halogen bonding, significantly influence crystal packing and molecular conformation.
- The presence of chlorine atoms in organic compounds can lead to unique non-covalent interactions.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title compound, C(15)H(13)Cl(2)NO(2).
- To investigate the conformational preferences and stabilizing forces within the crystal lattice.
- To characterize the nature and significance of a specific C-Cl⋯π interaction.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the compound.
- Analysis of the crystal structure involved measuring bond lengths, bond angles, and dihedral angles.
- Intermolecular interactions, including hydrogen bonds and halogen bonds, were identified and quantified.
Main Results:
- The crystal structure of C(15)H(13)Cl(2)NO(2) was successfully determined.
- A significant dihedral angle of 63.80° was observed between the two aromatic rings.
- A weak N-H⋯O hydrogen bond and a short C-Cl⋯π interaction (Cl⋯π separation of 3.5706 Å) were identified as key stabilizing forces.
Conclusions:
- The crystal packing of C(15)H(13)Cl(2)NO(2) is influenced by a combination of hydrogen bonding and halogen bonding interactions.
- The observed C-Cl⋯π interaction plays a role in the overall conformational stability of the molecule in the solid state.
- This structural characterization provides valuable insights into the solid-state chemistry of halogenated organic compounds.
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