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
N-(2,6-Dichloro-phen-yl)-3-methyl-benzamide
Summary
This study details the molecular structure of a novel compound, C(14)H(11)Cl(2)NO. The research reveals specific dihedral angles between its aromatic rings and amido group, with intermolecular hydrogen bonds forming crystal chains.
Area of Science:
- Organic Chemistry
- Crystallography
- Molecular Structure Analysis
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
- Crystallography provides a powerful method for determining precise molecular structures in the solid state.
- The specific compound, C(14)H(11)Cl(2)NO, presents an interesting case for structural analysis due to its substituted aromatic rings and amide linkage.
Purpose of the Study:
- To elucidate the detailed molecular structure of the title compound, C(14)H(11)Cl(2)NO.
- To quantify the spatial relationships between the aromatic rings and the central amido group.
- To investigate the intermolecular interactions governing the crystal packing.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided detailed geometric information.
- Identification of intermolecular interactions, such as hydrogen bonds, was performed.
Main Results:
- The molecular structure of C(14)H(11)Cl(2)NO was determined, revealing a dihedral angle of 70.9° between the two aromatic rings.
- The central amido group exhibited distinct dihedral angles of 26.6° and 82.5° with the methyl-phenyl and dichloro-phenyl rings, respectively.
- Intermolecular N-H⋯O hydrogen bonds were identified, leading to the formation of molecular chains along the c axis.
Conclusions:
- The study provides a precise description of the molecular conformation and crystal packing of C(14)H(11)Cl(2)NO.
- The observed dihedral angles highlight the non-planar nature of the molecule.
- The hydrogen bonding network plays a significant role in the self-assembly of these molecules in the solid state.
More Related Videos
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Related Concept Videos
01:37NMR Spectroscopy of Benzene Derivatives
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
01:23Nomenclature of Aromatic Compounds with a Single Substituent
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
01:11Nomenclature of Aromatic Compounds with Multiple Substituents
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
01:11Nucleophilic Aromatic Substitution: Elimination–Addition
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
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.
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...