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Related Concept Videos

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

3.3K
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.
3.3K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

1.9K
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...
1.9K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.2K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
3.2K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

1.9K
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.
1.9K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

3.9K
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.
3.9K
Nitrosation of Enols01:19

Nitrosation of Enols

9.9K
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.
9.9K

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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N-diazo-bridged nitroazoles: catenated nitrogen-atom chains compatible with nitro functionalities.

Ping Yin1, Damon A Parrish, Jean'ne M Shreeve

  • 1Department of Chemistry, University of Idaho, Moscow, Idaho, 83844-2343 (USA), Fax: (+1) 208-885-9146.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 26, 2014
PubMed
Summary

Researchers synthesized novel high-density energetic materials (HEDMs) using N-diazo-bridged azoles. These materials exhibit excellent stability and performance, offering a promising strategy for advanced energetic material design.

Keywords:
catenated nitrogen chainsenergetic propertiesexplosivesnitroazolesnitrogen

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Area of Science:

  • Chemistry
  • Materials Science
  • Energetic Materials

Background:

  • N-aminoazoles are precursors for energetic materials.
  • Oxidative coupling is a key synthetic strategy.
  • Nitrogen-rich compounds offer high energy density.

Purpose of the Study:

  • To synthesize novel N-diazo-bridged azoles.
  • To investigate the impact of nitrogen chain length on properties.
  • To develop advanced high-density energetic materials (HEDMs).

Main Methods:

  • Oxidative coupling of N-aminoazoles.
  • Incorporation of extended catenated nitrogen-atom chains and nitro groups.
  • Computational and experimental characterization of synthesized compounds.

Main Results:

  • Successful synthesis of N-diazo-bridged azoles with extended nitrogen chains.
  • Compounds exhibit high heats of formation, enhanced densities, and positive oxygen balances.
  • Achieved good detonation properties with excellent thermal stability and low impact sensitivity.
  • Demonstrated a balance between nitrogen chain length, performance, and stability.

Conclusions:

  • N-diazo-bridged azoles offer a viable route to HEDMs.
  • Optimizing nitrogen chain length is crucial for balancing performance and safety.
  • This strategy provides a promising pathway for designing next-generation energetic materials.