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Updated: May 10, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
(E)-N-(3,3-Di-phenyl-allyl-idene)-2-(tri-fluoro-meth-yl)aniline
Byung-Yong Yu1, Ji Eun Lee, Yong Seo Cho
1Advanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea.
Summary
This study details the crystal structure of a trifluoromethyl-substituted imine compound (C22H16F3N). Molecular conformation and intermolecular C-H⋯F hydrogen bonding were analyzed, revealing specific structural characteristics.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Imine compounds are versatile organic molecules with applications in synthesis and materials science.
- Understanding the conformational preferences and intermolecular interactions of imines is crucial for predicting their properties and designing new functional molecules.
- Fluorinated organic compounds often exhibit unique electronic and physical properties due to the high electronegativity of fluorine.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C22H16F3N.
- To determine the conformational details of the imine group and the orientation of the aromatic rings.
- To investigate the intermolecular interactions, specifically hydrogen bonding, present in the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the compound.
- Analysis of bond lengths, bond angles, and dihedral angles provided insights into the molecular geometry.
- Intermolecular interactions were identified and characterized using crystallographic analysis.
Main Results:
- The central imine group (C=N) was found to adopt an E conformation.
- Specific dihedral angles were measured between the 2-(trifluoromethyl)phenyl ring and the benzene rings (9.34(1)° and 68.8(1)°).
- A C-C-N=C torsion angle of 41.6(3)° was observed for the imine group. Weak C-H⋯F hydrogen bonds were identified, forming molecular chains parallel to the b-axis.
Conclusions:
- The crystal structure of C22H16F3N reveals a specific molecular conformation dictated by the imine geometry and aromatic ring orientations.
- The presence of weak C-H⋯F hydrogen bonds plays a significant role in the supramolecular assembly of the molecules in the solid state.
- This detailed structural information contributes to the understanding of structure-property relationships in fluorinated imine derivatives.
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01:17Nomenclature of Primary Amines
Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
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