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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
Diazonium Group Substitution: –OH and –H01:19

Diazonium 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.
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Basicity of Heterocyclic Aromatic Amines01:25

Basicity 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).
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium 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...

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Related Experiment Video

Updated: Jun 5, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Chloro-thia-zide-pyridine (1/3).

Andrea Johnston, Alastair J Florence, Alan R Kennedy

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary

    The crystal structure of 6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide reveals a 1:3 solvate with pyridine. This structure is notably stabilized by robust intermolecular hydrogen bonds.

    Area of Science:

    • Crystallography
    • Medicinal Chemistry
    • Organic Chemistry

    Background:

    • 6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide is a significant chemical entity.
    • Solvate formation is crucial in understanding compound stability and properties.

    Purpose of the Study:

    • To elucidate the crystal structure of the 1:3 solvate of 6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide with pyridine.
    • To identify the stabilizing interactions within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed.
    • The crystal structure was determined and analyzed for intermolecular interactions.

    Main Results:

    • The title compound, C(7)H(6)ClN(3)O(4)S(2)·3C(5)H(5)N, forms a 1:3 solvate with pyridine.

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    Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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    Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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    Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
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    Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines

    Published on: June 23, 2019

    Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
    14:11

    Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

    Published on: June 10, 2021

  • Strong intermolecular N-H⋯N hydrogen bonds were identified as the primary stabilizing force in the crystal structure.

    • Conclusions:

    • The pyridine tris-olvate of 6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide has a defined crystal structure.
    • Hydrogen bonding plays a critical role in the stabilization of this solvate.