Related Experiment Video
Updated: Jun 5, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
N-(2-Chloro-quinolin-3-ylmethyl-ene)aniline
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
This study details the crystal structure of a C(16)H(11)ClN(2) compound, revealing specific molecular arrangements and intermolecular interactions that stabilize its crystal packing. These findings contribute to understanding molecular assembly in crystalline solids.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the crystal structure of organic compounds is crucial for predicting their physical and chemical properties.
- Intermolecular interactions, such as hydrogen bonding and pi-stacking, play a significant role in crystal lattice formation.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(16)H(11)ClN(2).
- To investigate the specific molecular configuration and intermolecular forces governing its crystal packing.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed to determine the crystal structure.
- Analysis of bond lengths, bond angles, and intermolecular contacts (C-H⋯Cl, C-H⋯π, Cl⋯π) was performed.
Main Results:
- The compound exhibits a trans configuration around the C=N bond and a transoid arrangement involving the quinoline ring and azomethine carbon.
- Intra- and intermolecular interactions, including C-H⋯Cl, C-H⋯π, and Cl⋯π interactions (3.52 and 3.84 Å), were identified as key factors in crystal packing.
- A dihedral angle of 16.61(2)° was measured between the 2-chloro-quinoline and phenyl-amine planes.
Conclusions:
- The determined crystal structure provides a detailed molecular-level understanding of the compound's solid-state arrangement.
- The identified intermolecular interactions are essential for the stability and packing of the crystal structure.
- This structural information can guide the design of related compounds with tailored 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.
01:19Diazonium 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.
01:26Physical 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.
01:19Structure of Amines
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
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.
01:07Acid Halides to Amides: Aminolysis
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...