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

3.8K
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.
3.8K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.8K
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.
2.8K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.3K
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...
3.3K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

4.2K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
4.2K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

2.9K
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...
2.9K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

3.9K
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...
3.9K

You might also read

Related Articles

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

Sort by
Same author

The effect of base-pairing on the shape resonances of nucleobases.

The Journal of chemical physics·2026
Same author

Circumstellar Origin of Chrysene (C<sub>18</sub>H<sub>12</sub>) via Self-Recombination of Resonantly-Stabilized 1-Indenyl Radicals and Implications to the Aromaticity of the Carbonaceous Asteroid Ryugu.

Angewandte Chemie (International ed. in English)·2026
Same author

Effect of protein environment on the shape resonances of RNA pyrimidine nucleobases: Insights from a model system.

The Journal of chemical physics·2025
Same author

The Site of Azido Substitution in a Pyrimidine Nucleobase Dictates the Type of Nitrogen-Centered Radical Formed after Dissociative Electron Attachment.

The journal of physical chemistry. B·2025
Same author

Synthesis of Adenine Nucleosides with a Reactive (<i>β</i>-Iodovinyl)sulfone or (<i>β</i>-Keto)sulfone Group at the C2 Position and Their Polymerase-Catalyzed Incorporation into DNA.

Molecules (Basel, Switzerland)·2025
Same author

Azido derivatives of sesquiterpene lactones: Synthesis, anticancer proliferation, and chemistry of nitrogen-centered radicals.

Results in chemistry·2024

Related Experiment Video

Updated: Jun 25, 2025

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

8.4K

Nitrogen-Centered Radicals Derived from Azidonucleosides.

Yahaira Reyes1, Amitava Adhikary2, Stanislaw F Wnuk1

  • 1Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA.

Molecules (Basel, Switzerland)
|May 25, 2024
PubMed
Summary

Azido-modified nucleosides are key for click chemistry and metabolic labeling. This review details how their azido groups generate nitrogen-centered radicals (NCRs), exploring their chemistry and biological significance.

Keywords:
aminyl radicalsazidesiminyl radicalsnitrogen-centered radicalsnucleosidespurinespyrimidinesradiationradiosensitizersribonucleotide reductases

More Related Videos

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
11:04

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

3.0K
Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

3.0K

Related Experiment Videos

Last Updated: Jun 25, 2025

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

8.4K
Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
11:04

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

3.0K
Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

3.0K

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Biochemistry

Background:

  • Azido-modified nucleosides are versatile building blocks in chemical biology.
  • They serve as substrates for click chemistry and metabolic labeling of nucleic acids.
  • These compounds also hold potential as therapeutic agents and synthetic precursors.

Purpose of the Study:

  • To review the chemistry of azidonucleosides focusing on nitrogen-centered radical (NCR) generation.
  • To discuss the subsequent chemistry and biological implications of these NCRs.
  • To highlight the regio- and stereoselectivity of azido group incorporation and NCR generation.

Main Methods:

  • Review of literature on azidonucleoside chemistry.
  • Analysis of radical generation mechanisms under reductive and oxidative conditions.
  • Discussion of NCRs derived from radiation events and other precursors.

Main Results:

  • Azido groups in nucleosides can be selectively transformed into nitrogen-centered radicals (NCRs).
  • NCRs play critical roles in biological processes, such as enzyme inhibition (e.g., ribonucleotide reductases).
  • Reductive conditions for NCR generation often mimic radical species observed in radiation-induced events.

Conclusions:

  • Azidonucleosides are valuable precursors for generating NCRs with diverse chemical and biological applications.
  • Understanding NCR generation from azidonucleosides provides insights into radiation chemistry and drug development.
  • The review emphasizes the selective generation and reactivity of NCRs derived from azidonucleosides.