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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

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.
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...
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.
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.
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.
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

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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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Vanadyl Porphyrin Complex Functionalized with Nitronyl Nitroxide.

Anastasiya M Zimina1, Alexandr S Shmakov2,3, Andrey V Stepanov1

  • 1N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Ave. 47, 119991 Moscow, Russian Federation.

Inorganic Chemistry
|July 14, 2026
PubMed
Summary

Chemists created a new molecule linking a vanadyl (VO) unit and a nitronyl nitroxide radical. This self-assembling system forms dimers, enabling spin interactions for molecular quantum technologies.

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Area of Science:

  • Molecular Quantum Technologies
  • Supramolecular Chemistry
  • Organic Radical Chemistry

Background:

  • Effective coupling of chemically synthesized qubits is crucial for advancing molecular quantum technologies.
  • Vanadium(IV) (VO) magnetic centers show promise as molecular quantum units.

Purpose of the Study:

  • To synthesize and characterize the first vanadyl porphyrin derivative with a conjugated nitronyl nitroxide radical (VO(Por)-NN).
  • To investigate the self-organization and spin interactions in this novel vanadyl-containing system.

Main Methods:

  • Chemical synthesis and full characterization of the VO(Por)-NN complex.
  • X-ray diffraction (XRD) for determining molecular and crystal structures.
  • Electron paramagnetic resonance (EPR) spectroscopy to analyze spin interactions in solution and solid states.

Main Results:

  • The solvate complex VO(Por)-NN·n(CH2Cl2) was synthesized and structurally characterized.
  • In solution, EPR spectra showed both non-interacting monomeric VO(Por)-NN and interacting dimeric {VO(Por)-NN}2 species.
  • Desolvation of polycrystalline samples induced self-organization into the dimeric form, activating spin exchange interactions.

Conclusions:

  • A novel vanadyl porphyrin derivative featuring a conjugated nitronyl nitroxide radical was successfully synthesized.
  • The study demonstrates a unique self-organization mechanism leading to spin coupling in a vanadyl-organic radical system.
  • This represents a new supramolecular strategy for constructing multispin clusters for molecular quantum applications.