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Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic 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...

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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...

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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...

Diazonium Group Substitution: –OH and –H

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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.

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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...

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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.
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Updated: Jun 1, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

3,5-Dichloro-N-(2-methyl-but-3-yn-2-yl)benzamide.

Zong-Ling Ru¹, Guo-Xi Wang

¹Department of Chemical & Environmental Engineering, Anyang Institute of Technology, Anyang 455000, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

The crystal structure of a dichloro-amide compound reveals a twisted amide group relative to the benzene ring. Molecules self-assemble into one-dimensional chains through hydrogen bonding in the solid state.

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Published on: July 30, 2017

Area of Science:

Crystallography
Organic Chemistry
Supramolecular Chemistry

Background:

Understanding molecular conformation and intermolecular interactions is crucial in crystal engineering.
The study of amide-containing organic compounds provides insights into chemical bonding and material properties.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(12)H(11)Cl(2)NO.
To analyze the conformational properties of the amide group and its orientation relative to the benzene ring.
To investigate the intermolecular interactions governing the solid-state assembly of the molecules.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular and crystal structure.
Analysis of bond lengths, bond angles, and dihedral angles provided conformational details.
Intermolecular interactions, specifically hydrogen bonding, were identified and characterized.

Main Results:

The crystal structure of C(12)H(11)Cl(2)NO was successfully determined.
A significant dihedral angle of 31.98(2)° was observed between the amide group and the benzene ring, indicating a twisted conformation.
N-H⋯O hydrogen bonds were identified as the primary driving force for the formation of one-dimensional supramolecular chains.

Conclusions:

The title compound exhibits a non-planar conformation with a twisted amide moiety.
The crystal packing is dominated by N-H⋯O hydrogen bonds, leading to the formation of extended 1D supramolecular architectures.
This structural information contributes to the understanding of structure-property relationships in organic crystalline materials.