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Diazonium Group Substitution: –OH and –H

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.

Structure of Amines

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...

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

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...

Cholinergic Antagonists: Pharmacokinetics

Cholinergic Antagonists: Pharmacokinetics

Cholinergic antagonists—such as antimuscarinics—are available in oral, topical, ocular, parenteral, and inhalational formulations. Most antimuscarinics are oral formulations, while scopolamine is available as a topical patch, and ipratropium and tiotropium are available as inhalation aerosols or powders. Atropine, tropicamide, and cyclopentolate are topically instilled in the eye. Most antimuscarinics are lipid-soluble and readily absorbed from the gastrointestinal tract and the conjunctiva.

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

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.

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Related Experiment Video

Updated: Jun 5, 2026

Green Synthesis of Quinoline-Based Ionic Liquid

Green Synthesis of Quinoline-Based Ionic Liquid

Published on: September 27, 2024

8-(Carboxy-methoxy)-quinolinium nitrate monohydrate.

Feng Sun¹, Li Chen, Hua-Cai Fang

¹School of Chemistry and Environment, South China Normal University, Guangzhou 510631, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

The study reveals how a quinolinium salt and nitrate ions form square units through hydrogen bonds. These units then assemble into unique two-dimensional molecular layers.

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Green Synthesis of Quinoline-Based Ionic Liquid

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Facile Preparation of 4-Substituted Quinazoline Derivatives

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

Area of Science:

Crystal engineering
Supramolecular chemistry
Materials science

Background:

Understanding the self-assembly of organic salts is crucial for designing novel materials.
Hydrogen bonding plays a key role in directing the formation of ordered supramolecular structures.

Purpose of the Study:

To investigate the crystal structure and supramolecular assembly of an 8-carboxy-methoxy-quinolinium nitrate monohydrate.
To elucidate the role of hydrogen bonding in the formation of 2D layers.

Main Methods:

Single-crystal X-ray diffraction analysis was used to determine the molecular and crystal structure.
Analysis of intermolecular interactions, particularly hydrogen bonds, was performed.

Main Results:

The crystal structure consists of 8-carboxy-methoxy-quinolinium cations, nitrate anions, and water molecules.
These components dimerize via hydrogen bonds, forming square building-block units.
These units further assemble into gently undulating two-dimensional supramolecular layers.

Conclusions:

The study demonstrates a specific example of crystal engineering involving quinolinium salts.
Hydrogen bonding is confirmed as the primary driving force for the formation of the observed 2D supramolecular architecture.
The findings contribute to the understanding of crystal packing and the design of functional supramolecular materials.