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Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
N-Benzyl-2,3,4,5,6-penta-fluoro-benz-amide
Arto Valkonen1, Tanja Lahtinen, Kari Rissanen
1Nanoscience Center, Department of Chemistry, University of Jyväskylä, PO Box 35, FIN-40014 University of Jyväskylä, Finland.
This study details the crystal structure of a fluorinated organic compound, revealing how intermolecular forces like hydrogen bonds and pi-pi interactions stabilize its molecular arrangement.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the intermolecular forces governing crystal packing is crucial for predicting and controlling material properties.
- Fluorinated organic compounds exhibit unique electronic and structural characteristics.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(14)H(8)F(5)NO.
- To identify and analyze the intermolecular interactions responsible for crystal stabilization.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond distances, angles, and non-covalent interactions was performed.
Main Results:
- The crystal structure is stabilized by an intermolecular N-H⋯O hydrogen bond forming infinite chains.
- A dihedral angle of 18.34(5)° exists between the penta-fluorophenyl and phenyl rings.
- Weak C-H⋯O contacts and π-π interactions between phenyl rings further contribute to stability.
Conclusions:
- The crystal structure of C(14)H(8)F(5)NO is characterized by a combination of hydrogen bonding and π-π stacking.
- These interactions dictate the overall three-dimensional arrangement and stability of the crystal lattice.
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