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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.

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...

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...

Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

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.

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...

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Updated: May 18, 2026

Ammonia Synthesis at Low Pressure

Ammonia Synthesis at Low Pressure

Published on: August 23, 2017

Mechanism and kinetics for ammonium dinitramide (ADN) sublimation: a first-principles study.

R S Zhu¹, Hui-Lung Chen, M C Lin

¹Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.

The Journal of Physical Chemistry. A

|October 4, 2012

Summary

Quantum-mechanical calculations reveal a three-step sublimation mechanism for ammonium dinitramide (ADN). The study details the energy profiles for each step, providing insights into ADN decomposition pathways and sublimation kinetics.

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Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Ammonia Synthesis at Low Pressure

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Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on 14NH4+/15NH4+ Analyses via Sequential Conversion to N2O

Measurement of the Potential Rates of Dissimilatory Nitrate Reduction to Ammonium Based on ¹⁴NH₄⁺/¹⁵NH₄⁺ Analyses via Sequential Conversion to N₂O

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Area of Science:

Computational Chemistry
Materials Science
Chemical Physics

Background:

Understanding the sublimation and decomposition mechanisms of energetic materials like ammonium dinitramide (ADN) is crucial for safety and performance.
Previous studies have provided experimental data, but a detailed quantum-mechanical investigation of the ADN sublimation process was lacking.

Purpose of the Study:

To elucidate the quantum-mechanical mechanism of ammonium dinitramide (ADN) sublimation.
To calculate the energy profiles for each step of the sublimation/decomposition process.
To determine the sublimation and dissociation energies and rate constants.

Main Methods:

Generalized gradient approximation plane-wave density functional theory (DFT) calculations were employed.
A slab model with periodic boundary conditions was used to represent the solid ADN surface.
Lattice constants for bulk ADN were calculated and compared with experimental values.

Main Results:

A three-step mechanism for ADN sublimation was identified: surface relaxation, molecular complex sublimation, and complex dissociation.
Sublimation energy for the molecular complex was calculated as 29.4 kcal/mol, and dissociation energy of the complex was 13.9 kcal/mol.
The calculated total sublimation enthalpy (44.9 kcal/mol) agrees well with experimental and other theoretical predictions. Water molecules were found to increase ADN sublimation enthalpy.

Conclusions:

The study provides a detailed quantum-mechanical understanding of the ADN sublimation mechanism.
Calculated sublimation and dissociation energies, along with rate constants, align with experimental observations.
The findings offer valuable data for predicting the behavior and stability of ADN under various conditions.