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Updated: Jun 1, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2,2,2-Tribromo-N-(2-methyl-phen-yl)acetamide
Summary
This study reveals the crystal structure of a novel compound, C(9)H(8)Br(3)NO, detailing its molecular arrangement and hydrogen bonding patterns. The findings highlight specific intra-molecular and inter-molecular interactions within the crystal lattice.
Area of Science:
- Crystallography
- Chemical Physics
- Materials Science
Background:
- Understanding molecular interactions is crucial for predicting material properties.
- Crystal structure analysis provides fundamental insights into chemical bonding and intermolecular forces.
- The compound C(9)H(8)Br(3)NO presents an interesting case for studying hydrogen bonding networks.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(9)H(8)Br(3)NO.
- To identify and characterize intra-molecular and inter-molecular hydrogen bonding.
- To describe the packing arrangement of molecules within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the crystal structure.
- Analysis of bond lengths, bond angles, and intermolecular contacts was performed.
- Hydrogen bonding networks were identified using geometric criteria.
Main Results:
- The asymmetric unit contains two independent molecules of C(9)H(8)Br(3)NO.
- Intra-molecular N-H⋯Br hydrogen bonds were observed within each molecule.
- Inter-molecular N-H⋯O hydrogen bonds facilitate the formation of columnar chains in the crystal.
Conclusions:
- The crystal structure of C(9)H(8)Br(3)NO is characterized by specific intra- and inter-molecular hydrogen bonding.
- The observed hydrogen bonding dictates the columnar packing of molecules.
- This structural information is vital for understanding the compound's physical and chemical properties.
Related Concept Videos
01:19Amines to Amides: Acylation of Amines
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
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.
01:33Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
01:202° Amines to N-Nitrosamines: Reaction with NaNO2
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
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...
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