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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.

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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...

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

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.

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

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...

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Updated: May 19, 2026

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Published on: May 16, 2014

3,6-Diaza-octane-1,8-diaminium diiodide.

Ignacy Cukrowski¹, Adedapo S Adeyinka, David C Liles

¹Department of Chemistry, University of Pretoria, Private Bag X20, Hatfield 0028, South Africa.

Acta Crystallographica. Section E, Structure Reports Online

|August 21, 2012

Summary

This study details the crystal structure of a diammonium salt, revealing a unique kinked cation. This structure facilitates intermolecular hydrogen bonding with iodide anions, influencing crystal packing.

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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Published on: September 12, 2018

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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

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Published on: May 16, 2014

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Area of Science:

Crystal Chemistry
Supramolecular Chemistry
Materials Science

Background:

Understanding the crystal structures of organic salts is crucial for predicting their physical and chemical properties.
The role of hydrogen bonding in stabilizing crystal lattices is a fundamental concept in solid-state chemistry.

Purpose of the Study:

To elucidate the crystal structure of the title salt, C(6)H(20)N(4) (2+)·2I(-).
To investigate the intermolecular interactions, particularly hydrogen bonding, within the crystal lattice.
To analyze the conformational aspects of the diammonium dication.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of the crystal structure involved identifying hydrogen bonding networks and assessing cation conformation.

Main Results:

The asymmetric unit contains half of a symmetrical 3,6-diaza-octane-1,8-diaminium dication and an iodide anion.
A network of weak N-H⋯I intermolecular interactions was observed, involving ammonium and secondary amine groups with iodide anions.
The dication's backbone exhibits a 'kinked' conformation (torsion angle = 71.5(2)°), attributed to intramolecular hydrogen bonding.

Conclusions:

The crystal structure is stabilized by a combination of N-H⋯I hydrogen bonds and direct hydrogen bonding between adjacent cations.
The observed 'kinked' conformation of the dication is a key feature enabling these specific intermolecular interactions.
This study provides insights into the structure-property relationships in organic ammonium salts.