Sign In

19.23 : 1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

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 water loss to form nitrosonium ion. Nitrosonium ion is a highly reactive electrophile that undergoes a reaction with the nucleophilic nitrogen atom of an amine.

Nitrous acid can react with different classes of amines, such as primary, secondary, and tertiary aliphatic or aromatic amines, to give different products. For example, nitrous acid reacts with primary amines to form a diazonium salt. The reaction is called the diazotization of amines. Nitrous acid reacts with secondary amines to yield N-nitrosamine. With tertiary aliphatic amines, nitrous acid reacts to generate water-soluble salts and N-nitrosoammonium compounds. In contrast, tertiary arylamines undergo electrophilic aromatic substitution to form aromatic C-nitroso compounds.

Tags
DiazotizationNitrous AcidNitric AcidAmineDiazonium SaltAryldiazonium SaltN nitrosamineN nitrosoammoniumElectrophilic Aromatic SubstitutionC nitroso Compound

From Chapter 19:

article

Now Playing

19.23 : 1&deg; Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO<sub>2</sub> Overview

Amines

3.1K Views

article

19.1 : Amines: Introduction

Amines

3.8K Views

article

19.2 : Nomenclature of Primary Amines

Amines

3.0K Views

article

19.3 : Nomenclature of Secondary and Tertiary Amines

Amines

3.2K Views

article

19.4 : Nomenclature of Aryl and Heterocyclic Amines

Amines

2.0K Views

article

19.5 : Structure of Amines

Amines

2.2K Views

article

19.6 : Physical Properties of Amines

Amines

2.6K Views

article

19.7 : Basicity of Aliphatic Amines

Amines

5.3K Views

article

19.8 : Basicity of Aromatic Amines

Amines

6.6K Views

article

19.9 : Basicity of Heterocyclic Aromatic Amines

Amines

4.9K Views

article

19.10 : NMR Spectroscopy Of Amines

Amines

7.4K Views

article

19.11 : Mass Spectrometry of Amines

Amines

3.8K Views

article

19.12 : Preparation of Amines: Alkylation of Ammonia and Amines

Amines

2.9K Views

article

19.13 : Preparation of 1&deg; Amines: Azide Synthesis

Amines

3.6K Views

article

19.14 : Preparation of 1&deg; Amines: Gabriel Synthesis

Amines

3.2K Views

See More

JoVE Logo

Privacy

Terms of Use

Policies

Research

Education

ABOUT JoVE

Copyright © 2025 MyJoVE Corporation. All rights reserved