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Updated: May 22, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2,2,2-Trifluoro-N-(4-methyl-2-oxo-2H-chromen-7-yl)acetamide
1Key Laboratory of Natural Resources of Changbai Mountain & Functional Molecules (Yanbian University), Ministry of Eduction, Yanji 133002, People's Republic of China.
Summary
This study details the crystal structure of a molecule containing a trifluoromethyl group. Molecular interactions like hydrogen bonds and pi-pi stacking influence its crystal packing and arrangement.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding molecular interactions is crucial for predicting material properties.
- Crystal structure analysis reveals the three-dimensional arrangement of atoms and molecules.
- The title molecule, C(12)H(8)F(3)NO(3), possesses a trifluoromethyl group with potential implications for its physical and chemical behavior.
Purpose of the Study:
- To elucidate the crystal structure of the title molecule.
- To investigate the rotational disorder of the trifluoromethyl group.
- To identify and characterize intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and intermolecular contacts was performed.
- Rotational disorder was modeled and quantified.
Main Results:
- The trifluoromethyl group exhibits rotational disorder, adopting three distinct orientations with population ratios of 0.5:0.3:0.2.
- N-H⋯O hydrogen bonds link molecules into chains along the c-axis.
- π-π interactions between pyran rings (centroid-centroid distance = 3.462(4) Å) and short C⋯O contacts (3.149(4) Å) contribute to the crystal packing.
Conclusions:
- The crystal structure of C(12)H(8)F(3)NO(3) has been determined.
- The study highlights the significant role of rotational disorder and intermolecular forces in dictating crystal packing.
- These findings provide a foundation for understanding structure-property relationships in related fluorinated organic compounds.
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01:11Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
01:28Structures of Carboxylic Acid Derivatives
Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...