Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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.

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...

Preparation of 1° Amines: Azide Synthesis

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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...

Preparation and Reactions of Sulfides

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.

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...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

<i>catena</i>-Poly[[(5,5'-dimethyl-2,2'-bi-pyridine)nickel(II)]-μ<sub>2</sub>-azido-κ<sup>2</sup> <i>N</i>:<i>N</i>-μ<sub>2</sub>-azido-κ<sup>2</sup> <i>N</i>:<i>N</i>']: synthesis, crystal structure, Hirshfeld surface analysis and DFT calculations.

Acta crystallographica. Section E, Crystallographic communications·2025

Same author

<i>catena</i>-Poly[[(8-amino-quinoline)-cobalt(II)]-di-μ-azido].

IUCrData·2024

Same author

<i>trans</i>-Bis(2,2'-di-pyridyl-amine-κ<sup>2</sup> <i>N</i>,<i>N</i>')-bis-(1,1,3,3-tetra-cyano-2-eth-oxy-propenido-κ<i>N</i>)copper(II).

IUCrData·2023

Same author

Endogenous Bok is stable at the endoplasmic reticulum membrane and does not mediate proteasome inhibitor-induced apoptosis.

Frontiers in cell and developmental biology·2023

Same author

Concomitant dimorphism in poly[di-μ-azido-(5,5'-dimethyl-2,2'-bipyridine)iron(II)].

Acta crystallographica. Section C, Structural chemistry·2022

Same author

Detection of carfentanil in a cluster of patients without associated mortality: Response to Chhabra <i>et al.</i>

The American journal of drug and alcohol abuse·2021

Search research articles

Related Experiment Video

Updated: May 10, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Thio-phene-2-carbaldehyde azine.

David K Geiger¹, H Cristina Geiger, Laura M Szczesniak

¹Department of Chemistry, State University of New York-College at Geneseo, 1 College Circle, Geneseo, NY 14454, USA.

Acta Crystallographica. Section E, Structure Reports Online

|June 25, 2013

Summary

This summary is machine-generated.

The crystal structure of C10H8N2S2 was analyzed, revealing two independent molecules forming interlinked chains via weak C-H⋯π interactions. The structure was refined as a pseudo-merohedral twin, providing insights into molecular arrangement.

More Related Videos

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

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

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

Published on: July 17, 2020

Related Experiment Videos

Last Updated: May 10, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

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

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

Published on: July 17, 2020

Area of Science:

Crystallography
Solid-state chemistry
Supramolecular chemistry

Background:

The study focuses on the crystal structure of a specific organic compound, C10H8N2S2.
Understanding molecular packing and intermolecular interactions is crucial in solid-state chemistry.

Purpose of the Study:

To determine and describe the crystal structure of C10H8N2S2.
To investigate the intermolecular interactions governing the crystal packing.
To characterize the compound as a pseudo-merohedral twin.

Main Methods:

Single-crystal X-ray diffraction was employed to collect diffraction data.
The crystal structure was solved and refined using crystallographic software.
Twin refinement was performed using a specific twin law (001 0-10 100).

Main Results:

The asymmetric unit contains two independent half-molecules, each located on a center of symmetry.
Weak C-H⋯π interactions were identified as the primary forces linking molecules into chains along the [011] direction.
The crystal was successfully refined as a two-component pseudo-merohedral twin with domain fractions of 0.516(3) and 0.484(3).

Conclusions:

The crystal structure of C10H8N2S2 is characterized by specific molecular arrangements and intermolecular interactions.
The compound exhibits pseudo-merohedral twinning, a significant aspect for crystallographic analysis.
The findings contribute to the understanding of structure-property relationships in organic crystalline materials.