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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...

2° Amines to N-Nitrosamines: Reaction with NaNO2

2° Amines to N-Nitrosamines: Reaction with NaNO₂

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.

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.

Determining the pH of Salt Solutions

Determining the pH of Salt Solutions

The pH of a salt solution is determined by its component anions and cations. Salts that contain pH-neutral anions and the hydronium ion-producing cations form a solution with a pH less than 7. For example, in ammonium nitrate (NH4NO3) solution, NO3− ions do not react with water whereas NH4+ ions produce the hydronium ions resulting in the acidic solution. In contrast, salts that contain pH-neutral cations and the hydroxide ion-producing anions form a solution with a pH greater than 7. For...

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.

Preparation of Amines: Alkylation of Ammonia and Amines

Preparation of Amines: Alkylation of Ammonia and Amines

Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...

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Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

4-Methyl-anilinium nitrate.

¹Ordered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

The crystal structure of ammonium nitrate reveals zigzag chains formed by N-H⋯O hydrogen bonds between ammonium cations and nitrate anions. This arrangement dictates the compound's molecular architecture.

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Area of Science:

Crystallography
Solid-state chemistry
Materials science

Background:

Understanding the intermolecular interactions in ionic compounds is crucial for predicting their solid-state properties.
Ammonium nitrate (NH4NO3) is a widely used industrial chemical with diverse applications.
The precise arrangement of ions in crystal lattices influences material behavior.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(7)H(10)N(+)·NO(3) (-).
To identify and characterize the hydrogen bonding interactions present in the crystal lattice.
To describe the resulting supramolecular architecture formed by these interactions.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the atomic arrangement.
Analysis of hydrogen bonding networks was performed using crystallographic data.
Structural visualization tools were used to illustrate the observed molecular packing.

Main Results:

The crystal structure was solved and refined for the title compound, C(7)H(10)N(+)·NO(3) (-).
N-H⋯O hydrogen bonds were identified between the ammonium (NH4+) cations and nitrate (NO3-) anions.
These hydrogen bonds lead to the formation of one-dimensional zigzag chains propagating along the [100] direction.

Conclusions:

The crystal structure is stabilized by a network of N-H⋯O hydrogen bonds.
The hydrogen bonding pattern results in a specific supramolecular arrangement of zigzag chains.
This detailed structural information contributes to the understanding of ammonium nitrate's solid-state behavior.