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.
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...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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...

You might also read

Related Articles

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

Sort by
Same author

Synthesis of oleanonic acid derivatives and evaluation of their biological activities.

Natural product research·2026
Same author

Caffeoylquinic acid derivatives isolated from <i>Tussilago farfara</i> L. as potential anti-leishmanial agents; <i>in vitro</i> and <i>in silico</i> studies.

Natural product research·2026
Same author

Microbial catalyzed derivatization of canrenone with Glomerella fusarioides, and Cunninghamella blakesleeana, and evaluation of aromatase inhibitory activity of the resulting metabolites.

Steroids·2025
Same author

Abnormal Biochemical Parameters of Macro- and Microvascular Complications in Diabetic Patients at the Bafoussam Regional Hospital of the West Region, Cameroon.

Cureus·2025
Same author

Hyperhelianthemones A-D: Polycyclic polyprenylated benzoylphloroglucinols from Hypericum helianthemoides.

Phytochemistry·2025
Same author

Identification of new potential inhibitors of pteridine reductase-1 (PTR1) via biophysical and biochemical mechanism-based approaches: Step towards the treatment of Leishmaniasis.

International journal of biological macromolecules·2024
Same journal

Crystal structure of 1-(piperidin-1-yl)butane-1,3-dione.

Acta crystallographica. Section E, Structure reports online·2015
Same journal

Crystal structure of methyl 1-methyl-3,5-diphenyl-7-tosyl-3,6,7,11b-tetra-hydro-pyrazolo-[4',3':5,6]pyrano[3,4-c]quinoline-5a(5H)-carboxyl-ate.

Acta crystallographica. Section E, Structure reports online·2015
Same journal

Crystal structure of 4-amino-1-(4-methyl-benz-yl)pyridinium bromide.

Acta crystallographica. Section E, Structure reports online·2015
Same journal

Crystal structure of (Z)-3-benz-yloxy-6-[(2-hy-droxy-anilino)methyl-idene]cyclo-hexa-2,4-dien-1-one.

Acta crystallographica. Section E, Structure reports online·2015
Same journal

Crystal structure of bis-(1-benzyl-1H-1,2,4-triazole) perchloric acid monosolvate.

Acta crystallographica. Section E, Structure reports online·2015
Same journal

Crystal structure of 2-(di-phenyl-phos-phanyl)phenyl 4-(hy-droxy-meth-yl)benzoate.

Acta crystallographica. Section E, Structure reports online·2015
See all related articles

Related Experiment Video

Updated: May 27, 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

(3Z)-3-Hydrazinylideneindolin-2-one.

Rifat Ara Jamal, Uzma Ashiq, Sammer Yousuf

    Acta Crystallographica. Section E, Structure Reports Online
    |November 8, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study reveals the molecular structure of C(8)H(7)N(3)O, highlighting its near-planar shape and stabilization through intra- and inter-molecular hydrogen bonds, forming zigzag sheets in the crystal lattice.

    More Related Videos

    Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
    11:45

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

    Published on: August 22, 2018

    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

    Related Experiment Videos

    Last Updated: May 27, 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

    Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
    11:45

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

    Published on: August 22, 2018

    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

    Area of Science:

    • Crystallography
    • Molecular Chemistry

    Background:

    • Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
    • Hydrogen bonding and π-π interactions are key non-covalent forces that dictate crystal packing and material properties.

    Purpose of the Study:

    • To elucidate the crystal structure and intermolecular interactions of the title molecule, C(8)H(7)N(3)O.
    • To investigate the role of hydrogen bonding and π-π stacking in the self-assembly of this compound.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the precise atomic arrangement.
    • Analysis of bond lengths, bond angles, and non-covalent interactions (hydrogen bonds, π-π stacking) was performed.

    Main Results:

    • The title molecule, C(8)H(7)N(3)O, exhibits a nearly planar conformation with a maximum deviation of 0.0232(2) Å from the least-squares plane.
    • An intramolecular N-H⋯O hydrogen bond stabilizes the Z conformation of the C=N double bond.
    • Intermolecular N-H⋯N and N-H⋯O hydrogen bonds link adjacent molecules into zigzag sheets parallel to the c axis.
    • These sheets are further stabilized by π-π interactions with a centroid-centroid distance of 3.7390(10) Å.

    Conclusions:

    • The crystal structure of C(8)H(7)N(3)O is characterized by a combination of intramolecular and intermolecular hydrogen bonding, leading to a 2D sheet architecture.
    • π-π interactions play a significant role in reinforcing the stability of these molecular sheets.
    • The findings provide insights into the structure-property relationships of this class of organic compounds.