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

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

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

2° Amines to N-Nitrosamines: Reaction with NaNO2

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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.
4.7K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.0K
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.
3.0K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

4.2K
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.
4.2K
NMR Spectroscopy Of Amines01:19

NMR Spectroscopy Of Amines

9.7K
In proton NMR spectroscopy, primary amines and secondary amines showcase their N–H protons as a broad signal in the chemical shift range between δ 0.5 and 5 ppm. The exact position in this range depends on several factors, including sample concentration, hydrogen bonding, and the type of solvent used. Since amine protons undergo fast proton exchange in solution, the protons are labile and therefore do not participate in any splitting with adjacent protons. Thus, the observed peak is...
9.7K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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4.2K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Azanone (HNO): generation, stabilization and detection.

Cecilia Mariel Gallego1, Agostina Mazzeo1, Paola Vargas1

  • 1Departamento de Química Inorgánica, Analítica, y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, INQUIMAE-CONICET, Ciudad Universitaria Pab. 2 C1428EHA Buenos Aires Argentina doctorovich@qi.fcen.uba.ar.

Chemical Science
|August 27, 2021
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Summary
This summary is machine-generated.

Nitroxyl (HNO), a reactive nitrogen species, is challenging to study due to its instability. This work reviews methods for its detection and explores recent advances in understanding its endogenous generation.

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Area of Science:

  • Chemistry
  • Biochemistry
  • Reactive Nitrogen Species

Background:

  • Nitroxyl (HNO), also known as azanone, was recognized as a biologically relevant reactive nitrogen species in the 2000s.
  • HNO is highly reactive and unstable, making direct study difficult.
  • Its chemistry and effects are typically investigated using donor compounds that release HNO upon stimulation.

Purpose of the Study:

  • To critically compare various detection strategies for HNO in chemical and biological systems.
  • To review recent advances in the understanding of endogenous HNO generation.
  • To discuss methods for stabilizing HNO and its conjugate base through metal coordination.

Main Methods:

  • Utilizing donor compounds to generate HNO in solution and gas phases.
  • Employing metal coordination with ligands (e.g., metalloporphyrins, pincer ligands) to stabilize HNO.
  • Reviewing and comparing diverse detection techniques: colorimetric assays, EPR, HPLC, mass spectrometry, fluorescent probes, and electrochemical analysis.

Main Results:

  • Several strategies for HNO detection have been developed and are critically evaluated.
  • Advances in stabilizing HNO through metal complexation have been explored.
  • Significant progress has been made in the last decade regarding endogenous HNO generation.

Conclusions:

  • The high reactivity and instability of HNO necessitate indirect study methods and specialized detection techniques.
  • Coordination chemistry offers a route to stabilize this elusive species.
  • Recent research highlights the growing evidence and understanding of HNO's endogenous production in biological systems.