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Updated: Jun 1, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
4-Chloro-N-(pyrimidin-2-yl)aniline.
A Bakar Maizathul Akmam1, Zanariah Abdullah, Seik Weng Ng
1Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia.
Summary
This study details the crystal structure of a chlorinated nitrogen-containing compound, C(10)H(8)ClN(3). Researchers observed specific bond angles and the formation of hydrogen-bonded dimers in the solid state.
Area of Science:
- Crystallography
- Chemical Physics
- Organic Chemistry
Background:
- Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
- Aromatic and heterocyclic compounds containing nitrogen and chlorine are important in medicinal chemistry and materials science.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title compound, C(10)H(8)ClN(3).
- To analyze the geometric parameters, specifically the N-atom bond angle, and hydrogen bonding patterns.
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.
Main Results:
- The title compound, C(10)H(8)ClN(3), exhibits a planar N atom with an angle of 128.00(12)° due to the presence of two aromatic rings.
- A significant intermolecular hydrogen bond was identified between the amino N atom of one molecule and the pyrimidyl N atom of a neighboring molecule.
- These interactions lead to the formation of a centrosymmetric hydrogen-bonded dimer in the crystal lattice.
Conclusions:
- The crystal structure reveals specific molecular geometry and intermolecular forces governing the solid-state arrangement.
- The observed hydrogen bonding pattern is a key factor in the self-assembly of these molecules into dimers, influencing bulk properties.
Related Concept Videos
01:10Nomenclature of Aryl and Heterocyclic Amines
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
01:26Physical Properties of Amines
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
01:07Preparation of Acid Anhydrides
One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
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.
01:19Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
01:28Preparation of 1° Amines: Gabriel Synthesis
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...