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

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

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

5.2K
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.
5.2K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.5K
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.
3.5K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

9.6K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
9.6K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

4.0K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
4.0K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

7.0K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
7.0K
Nitrosation of Enols01:19

Nitrosation of Enols

10.6K
The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
10.6K

You might also read

Related Articles

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

Sort by
Same author

Questioning the Usefulness of Stimulation Rate Changes to Optimize Perception in Cochlear Implant Users.

Audiology research·2026
Same author

Thermal Polymerization of Softwood Kraft Lignin: Enhanced Adhesion of Lignin-Phenol-Formaldehyde Blends.

ACS omega·2025
Same author

Methylation of softwood and hardwood kraft lignins with chloromethane.

RSC advances·2024
Same author

Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds.

The Journal of organic chemistry·2023
Same author

Seeking Rules Governing Mixed Molecular Crystallization.

Crystal growth & design·2023
Same author

Diphenoquinhydrones and Related Hydrogen-Bonded Charge-Transfer Complexes.

The Journal of organic chemistry·2022

Related Experiment Video

Updated: Mar 28, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.8K

Dimerization of Aromatic C-Nitroso Compounds.

Daniel Beaudoin1, James D Wuest1

  • 1Département de Chimie, Université de Montréal , Montréal, Québec H3C 3J7, Canada.

Chemical Reviews
|January 6, 2016
PubMed
Summary

Aromatic nitroso compounds reversibly dimerize to form azodioxy compounds. This review comprehensively analyzes this phenomenon, covering structures, mechanisms, and influencing factors in C-nitroso chemistry.

Area of Science:

  • Organic Chemistry
  • Physical Chemistry

Background:

  • Aromatic C-nitroso compounds (Ar-N═O) exhibit unique reversible dimerization.
  • This property forms azodioxy compounds, a subject of ongoing research interest.

Purpose of the Study:

  • To provide a comprehensive analysis of the reversible dimerization of aromatic nitroso compounds.
  • To summarize current knowledge and stimulate further research in C-nitroso chemistry.

Main Methods:

  • Literature review and synthesis of existing research on nitrosoarene dimerization.
  • Detailed examination of structural, mechanistic, thermodynamic, and kinetic aspects.

Main Results:

  • Detailed analysis of monomeric and dimeric structures.
  • Exploration of factors influencing dimerization (thermodynamic, kinetic, environmental).

More Related Videos

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.8K
A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
07:38

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

Published on: September 25, 2017

10.8K

Related Experiment Videos

Last Updated: Mar 28, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.8K
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.8K
A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
07:38

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s

Published on: September 25, 2017

10.8K
  • Discussion of the behavior of dinitroso and polynitroso compounds.

    • Conclusions:

    • Reversible dimerization is a key characteristic of aromatic nitroso compounds.
    • Understanding this phenomenon is crucial for advancing C-nitroso chemistry and its applications.