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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

4.1K
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...
4.1K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.5K
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.
3.5K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

5.0K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
5.0K
Nitriles to Carboxylic Acids: Hydrolysis01:08

Nitriles to Carboxylic Acids: Hydrolysis

5.6K
Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
5.6K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

5.4K
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.
5.4K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

5.2K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
5.2K

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Updated: Apr 17, 2026

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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Design concept for α-hydrogen-substituted nitroxides.

Michal Amar1, Sukanta Bar1, Mark A Iron2

  • 1Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, 32000 Haifa, Israel.

Nature Communications
|February 7, 2015
PubMed
Summary
This summary is machine-generated.

Researchers developed stable cyclic α-hydrogen nitroxides, overcoming inherent instability. A novel design strategy using a γ-position substituent prevents disproportionation, enabling new applications for these vital nitroxyl radicals.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Biochemistry

Background:

  • Stable nitroxides (nitroxyl radicals) are crucial in chemistry, biology, and medicine.
  • Understanding factors affecting nitroxide stability is key for developing new compounds.
  • Existing stable nitroxides often have bulky tertiary alkyl groups, limiting their utility.

Purpose of the Study:

  • To introduce a novel design concept for stable cyclic α-hydrogen nitroxides.
  • To demonstrate a facile synthesis of new, stable α-hydrogen nitroxides.
  • To elucidate the stabilizing mechanisms of these novel nitroxides.

Main Methods:

  • Synthesis and characterization of two diverse series of cyclic α-hydrogen nitroxides.
  • Investigating the role of a γ-position substituent on nitroxide stability.
  • Computational studies to analyze disproportionation pathways.

Main Results:

  • Successfully synthesized and characterized novel, stable cyclic α-hydrogen nitroxides.
  • Demonstrated that a co-planar substituent at the γ-position is critical for stability.
  • Computational analysis confirmed that steric and stereoelectronic effects preclude disproportionation.

Conclusions:

  • A new design strategy for stable α-hydrogen nitroxides has been established.
  • The presence of a γ-position substituent effectively enhances nitroxide stability.
  • These findings pave the way for the development of new nitroxide-based therapeutics and chemical tools.