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Updated: Jun 1, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2,6-Bis(trifluoro-meth-yl)benzoic acid.
1Department of Chemistry, Saint Mary's University, 923 Robie Street, Halifax, NS, Canada B3H 3C3.
Summary
This study details the crystal structure of a fluorinated organic compound, revealing molecular disorder and specific dihedral angles. Intermolecular hydrogen bonding forms a catemeric structure, impacting its solid-state arrangement.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
- Fluorinated organic molecules offer unique electronic and steric properties relevant to various applications.
- Crystal structure analysis provides detailed insights into molecular arrangement and intermolecular interactions.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(9)H(4)F(6)O(2).
- To characterize the molecular geometry, including dihedral angles and the presence of disorder.
- To investigate the intermolecular interactions, specifically hydrogen bonding, that dictate the compound's supramolecular assembly.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional arrangement of atoms.
- Crystallographic data were analyzed to identify the number of independent molecules, disorder, and bond parameters.
- Intermolecular interactions, such as hydrogen bonds, were identified and analyzed using geometric criteria.
Main Results:
- The asymmetric unit contains two independent molecules of C(9)H(4)F(6)O(2).
- One molecule exhibits positional disorder in its trifluoromethyl groups.
- Dihedral angles between the benzene ring and carboxyl group range from 71.5(2)° to 99.3(2)°.
- A catemeric structure is formed through intermolecular O-H⋯O hydrogen bonding between carboxyl groups.
Conclusions:
- The crystal structure of C(9)H(4)F(6)O(2) is characterized by molecular disorder and specific conformational preferences.
- Intermolecular hydrogen bonding plays a significant role in organizing the molecules into a catemeric supramolecular architecture.
- These findings contribute to the understanding of structure-property relationships in fluorinated organic compounds.
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