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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
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
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.
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Inorganic Nitrogen Assimilation01:22

Inorganic Nitrogen Assimilation

938
Nitrogen is an essential element in biological systems, forming a crucial component of proteins, nucleic acids, and other cellular constituents. Many bacteria and archaea acquire nitrogen in the form of nitrate (NO₃⁻) or ammonia (NH₃), which are then assimilated into biomolecules through specific enzymatic pathways.Assimilatory Nitrate ReductionWhen nitrate enters the cell, it undergoes a two-step reduction process known as assimilatory nitrate reduction. Initially, the enzyme...
938
Nitriles to Ketones: Grignard Reaction00:57

Nitriles to Ketones: Grignard Reaction

6.9K
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the...
6.9K
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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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Published on: April 27, 2017

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Insensitive nitrogen-rich materials incorporating the nitroguanidyl functionality.

Qinghua Zhang1, Chunlin He, Ping Yin

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

Chemistry, an Asian Journal
|October 24, 2013
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel nitroguanidyl-functionalized, nitrogen-rich energetic materials from triazine and tetrazine derivatives. Some compounds show performance comparable to RDX, indicating potential applications.

Keywords:
nitrogen heterocyclesnitrogen-rich materialsnitroguanidyl functionalitysensitivitytetrazinetriazine

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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
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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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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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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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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Energetic Materials

Background:

  • Nitrogen-rich compounds are of interest for energetic materials.
  • 1,3,5-triazine and 1,2,4,5-tetrazine scaffolds offer high nitrogen content.

Purpose of the Study:

  • To synthesize and characterize a new class of nitroguanidyl-functionalized nitrogen-rich materials.
  • To evaluate the energetic performance of these novel compounds.

Main Methods:

  • Synthesis via reactions of N-nitroso-N'-alkylguanidines with hydrazine derivatives of triazine/tetrazine.
  • Characterization using NMR, IR spectroscopy, elemental analysis, and DSC.
  • Computational calculation of heats of formation and experimental density to determine detonation properties.

Main Results:

  • Successful synthesis of nitroguanidyl-functionalized nitrogen-rich compounds.
  • Comprehensive characterization confirming the structures and thermal properties.
  • Energetic performance (detonation pressure and velocity) comparable to RDX was observed for some synthesized materials.

Conclusions:

  • A new class of promising energetic materials based on triazine and tetrazine has been developed.
  • The synthesized compounds exhibit high energetic performance, suggesting potential for practical applications.
  • Further research into these materials could lead to advanced energetic formulations.