Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

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.
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature 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.
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.
Physical Properties of Amines01:26

Physical 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.
Preparation of 1° Amines: Azide Synthesis01:22

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...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.

You might also read

Related Articles

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

Sort by
Same author

Next-generation polydopamine nanocoatings advancing the understanding of surface properties and antimicrobial efficacy.

Scientific reports·2026
Same author

Mixed Matrix Membranes Containing Green Synthesized Poly(MBAAm-<i>co</i>-VSPI) Zwitterionic Nanoparticles for the Removal of Reactive Dyes.

ACS omega·2025
Same author

Exploring the biological activity and setting dynamics of a novel polydopamine-based root repair material.

Journal of oral biology and craniofacial research·2025
Same author

Efficient multi-pollutant removal: The role of Keggin polyoxometalates in polysulfone-chitosan blend membranes.

International journal of biological macromolecules·2025
Same author

Synthesis of N-heterocyclic carbene‑selenium complexes modulating apoptosis and autophagy in cancer cells: Probing the interactions with biomolecules and enzymes.

Bioorganic chemistry·2025
Same author

Enhanced Cartilage Regeneration: Chemical, Mechanical, and In Vitro Analysis of Innovative TiO<sub>2</sub>-Reinforced PVA Implants.

ACS omega·2025

Related Experiment Video

Updated: Jun 2, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

4-(1,2,4-Triazol-1-yl)aniline.

Hoong-Kun Fun, Ching Kheng Quah, B Chandrakantha

    Acta Crystallographica. Section E, Structure Reports Online
    |April 28, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the crystal structure of a C8H8N4 compound, revealing a 34.57° dihedral angle between its triazole and benzene rings. Molecules form sheets via hydrogen bonds and exhibit aromatic π-π stacking.

    More Related Videos

    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
    06:34

    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

    Published on: June 20, 2014

    Related Experiment Videos

    Last Updated: Jun 2, 2026

    Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
    08:43

    Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

    Published on: January 19, 2016

    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
    06:34

    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

    Published on: June 20, 2014

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Supramolecular Chemistry

    Background:

    • Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
    • Molecular interactions, such as hydrogen bonding and π-π stacking, significantly influence crystal packing and material characteristics.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C8H8N4.
    • To analyze the intermolecular interactions governing the compound's solid-state assembly.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of hydrogen bonding (N-H⋯N, C-H⋯N) and π-π stacking interactions was performed.

    Main Results:

    • The dihedral angle between the triazole and benzene rings was determined to be 34.57(7)°.
    • Molecules are arranged in sheets parallel to the ac plane through intermolecular hydrogen bonds.
    • Aromatic π-π stacking (centroid-centroid distance = 3.6750(8) Å) and N-H⋯π interactions were identified.

    Conclusions:

    • The crystal structure of C8H8N4 is characterized by a specific dihedral angle between its aromatic rings.
    • Intermolecular hydrogen bonding and π-π stacking are key factors in the observed sheet-like crystal packing.