Related Experiment Video
Updated: Jun 1, 2026
11:01
Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
3-Anilino-N-p-tolyl-benzamide
Xing-Xing Yang1, Guan-Feng Liu, Da-Bin Qin
1School of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China.
Summary
This study details the crystal structure of a C(20)H(18)N(2)O compound, revealing distinct molecular conformations stabilized by intramolecular hydrogen bonds. Intermolecular interactions form crystal chains, offering insights into molecular assembly.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- The title compound, C(20)H(18)N(2)O, possesses a structure comprising three aromatic rings.
- Crystallization reveals two independent molecules (A and B) within the asymmetric unit.
Purpose of the Study:
- To elucidate the three-dimensional structure and conformational characteristics of the title compound.
- To investigate the intermolecular interactions governing crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of dihedral angles and hydrogen bonding patterns provided insights into molecular conformation and crystal assembly.
Main Results:
- Two independent molecules (A and B) exhibit slightly different conformations, characterized by varying dihedral angles between aromatic rings.
- Intramolecular N-H⋯O hydrogen bonds stabilize the individual molecular structures.
- Intermolecular N-H⋯O hydrogen bonds link molecules into chains propagating along the [010] direction.
- C-H⋯π interactions were also observed in the crystal lattice.
Conclusions:
- The study provides a detailed structural characterization of the C(20)H(18)N(2)O compound.
- The observed hydrogen bonding and C-H⋯π interactions are key factors in the compound's crystal packing and supramolecular assembly.
More Related Videos
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.
01:19Structure 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...
01:20Electrophilic Aromatic Substitution: Nitration of Benzene
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
01:23Amines to Sulfonamides: The Hinsberg Test
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
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.