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Updated: Jun 1, 2026
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
N-(Pyrimidin-2-yl)aniline.
Edura Badaruddin1, Nasir Shah Bakhtiar, Zaharah Aiyub
1Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia.
Summary
This study details the crystal structure of a C(10)H(9)N(3) compound, revealing two independent molecules. These molecules form dimers through hydrogen bonds in the crystal lattice.
Area of Science:
- Crystallography
- Molecular structure determination
- Organic chemistry
Background:
- Understanding molecular arrangements is crucial in chemistry.
- Crystal structure analysis provides detailed insights into intermolecular interactions.
- The compound C(10)H(9)N(3) represents a class of molecules with potential applications.
Purpose of the Study:
- To elucidate the crystal structure of the title compound C(10)H(9)N(3).
- To analyze the molecular geometry, including inter-ring dihedral angles and bond angles.
- To investigate intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed.
- The asymmetric unit was analyzed to determine molecular conformation.
- Hydrogen bonding interactions were identified and characterized.
Main Results:
- Two independent molecules of C(10)H(9)N(3) were found in the asymmetric unit.
- Inter-ring dihedral angles were measured as 31.1(1)° and 35.3(1)°.
- Bridging C-N-C bond angles were determined to be 128.2(1)° and 129.1(1)°.
- The two independent molecules form a dimer via two N-H⋯N hydrogen bonds in the crystal.
Conclusions:
- The crystal structure of C(10)H(9)N(3) has been successfully determined.
- The presence of two independent molecules and their specific dihedral angles are key structural features.
- Intermolecular hydrogen bonding plays a significant role in the crystal packing.
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.
01:25Basicity of Heterocyclic Aromatic Amines
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
01:18Basicity of Aromatic Amines
The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
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.
01:17Nomenclature 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.