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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...

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.

Structure of Conjugated Dienes

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...

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.

Diels–Alder Reaction: Characteristics of Dienes

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...

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.

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Updated: May 26, 2026

Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups

Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups

Published on: February 11, 2012

Decane-1,10-diaminium dinitrate.

Charmaine Arderne¹

¹University of Johannesburg, Department of Chemistry, PO Box 524, Auckland Park, Johannesburg 2006, South Africa.

Acta Crystallographica. Section E, Structure Reports Online

|January 6, 2012

Summary

The crystal structure of a nitrogen-containing compound reveals a unique double zigzag arrangement of dications. This structure is stabilized by nitrate anions and extensive hydrogen bonding.

Area of Science:

Crystal Engineering
Supramolecular Chemistry
Materials Science

Background:

Understanding the packing arrangements of organic dications is crucial for designing novel materials.
Nitrate anions are common counterions that can influence crystal packing through electrostatic interactions and hydrogen bonding.
Hydrogen bonding plays a significant role in stabilizing crystal structures and directing molecular assembly.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(10)H(26)N(2) (2+)·2NO(3) (-).
To analyze the packing arrangement of the dications and their interaction with nitrate anions.
To investigate the hydrogen bonding network within the crystal structure.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional crystal structure.

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

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Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups

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

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

Analysis of intermolecular interactions, including hydrogen bonds and electrostatic contacts, was performed.

Main Results:

The crystal structure displays a distinctive back-to-back paired double-stacked packing of dications, forming an overall double zigzag pattern.
Each dication pair is encircled by a ring of ten nitrate anions.
A complex three-dimensional hydrogen bonding network involving N-H···O and N-H···(O,O) interactions was identified.

Conclusions:

The study reveals a novel supramolecular architecture driven by dication stacking and anion interactions.
The intricate hydrogen bonding network is key to the stability of the observed crystal structure.
This detailed structural analysis provides insights into the self-assembly principles for related organic salts.