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Related Concept Videos

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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 Mechanism01:37

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.
Diazonium Group Substitution: –OH and –H01:19

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.
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

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.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Nitrosation of Enols01:19

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

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Recording Gamma Band Oscillations in Pedunculopontine Nucleus Neurons
09:04

Recording Gamma Band Oscillations in Pedunculopontine Nucleus Neurons

Published on: September 14, 2016

4-Nitramino-3,5-dinitropyrazole-based energetic salts.

Yanqiang Zhang1, Damon A Parrish, Jean'ne M Shreeve

  • 1Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 16, 2011
PubMed
Summary
This summary is machine-generated.

Researchers synthesized 14 new nitrogen-rich energetic salts from 4-nitramino-3,5-dinitropyrazole. These compounds exhibit properties comparable to RDX and TATB, indicating their potential as high-energy materials.

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Area of Science:

  • Energetic materials science
  • Organic synthesis
  • Materials chemistry

Background:

  • The development of novel energetic materials is crucial for advancements in various fields.
  • Nitrogen-rich compounds offer high energy density and potentially improved safety characteristics.

Purpose of the Study:

  • To synthesize and characterize new nitrogen-rich energetic salts.
  • To evaluate the energetic properties and safety of the synthesized compounds.

Main Methods:

  • Synthesis of 4-nitramino-3,5-dinitropyrazole and its ammonium salt.
  • Metathesis reactions with selected cations to yield 14 energetic salts.
  • Characterization using NMR, IR spectroscopy, elemental analysis, and X-ray diffraction.
  • Evaluation of thermal stability, detonation properties, and impact sensitivity.

Main Results:

  • Successful synthesis of 14 nitrogen-rich energetic salts in high yield.
  • Structural confirmation of key salts via single-crystal X-ray diffraction.
  • Demonstrated high decomposition temperatures (115-229 °C), detonation pressures (23.27-37.42 GPa), and detonation velocities (7713-9013 m/s).
  • Exhibited impact sensitivities ranging from 5-40 J.

Conclusions:

  • The synthesized 4-nitramino-3,5-dinitropyrazolate salts possess excellent energetic properties.
  • These salts demonstrate performance comparable to established energetic materials like RDX and TATB.
  • The findings suggest significant potential for these novel compounds in energetic applications.