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Related Concept Videos

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

2° Amines to N-Nitrosamines: Reaction with NaNO2

4.8K
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.
4.8K
Radical Autoxidation01:20

Radical Autoxidation

2.6K
The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
2.6K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

4.2K
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,...
4.2K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

3.5K
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...
3.5K
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
Nitrosation of Enols01:19

Nitrosation of Enols

5.8K
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.
5.8K

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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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Nitroxides as Building Blocks for Nanoantioxidants.

Damiano Genovese1, Andrea Baschieri2, Danilo Vona3

  • 1Department of Chemistry "Giacomo Ciamician", University of Bologna, via Selmi 2, 40126 Bologna, Italy.

ACS Applied Materials & Interfaces
|June 22, 2021
PubMed
Summary

Novel nanoantioxidants were developed using Pluronic-silica nanoparticles (PluS) with bound nitroxide moieties. These nanoantioxidants demonstrated significantly enhanced radical trapping antioxidant activity and longer inhibition duration compared to molecular analogues.

Keywords:
antioxidantlipid peroxidationnanoparticlesnitroxidesperoxyl radicalsproton-coupled electron transfer

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Area of Science:

  • Chemistry
  • Materials Science
  • Biochemistry

Background:

  • Nitroxides are effective radical trapping antioxidants crucial for scavenging peroxyl (ROO•) radicals.
  • Their biological activity is directly linked to their efficiency in radical scavenging.
  • Understanding the structure-activity relationship of nitroxide derivatives is key to developing potent antioxidants.

Purpose of the Study:

  • To synthesize and characterize Pluronic-silica nanoparticles (PluS) functionalized with nitroxide moieties (PluS-NO).
  • To evaluate the radical scavenging rate constants (k_inh) of various 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) derivatives and PluS-NO.
  • To compare the antioxidant efficacy and inhibition duration of PluS-NO nanoantioxidants with their molecular analogues.

Main Methods:

  • Kinetic measurements of peroxyl radical scavenging rate constants (k_inh) for TEMPO derivatives.
  • Synthesis of Pluronic-silica nanoparticles (PluS) with covalently bound nitroxide groups (PluS-NO) and embedded coumarin dyes.
  • Characterization of PluS-NO nanoparticles and comparison of their antioxidant performance against free nitroxides.

Main Results:

  • Rate constants (k_inh) for TEMPO derivatives varied based on substituents, with a Marcus relationship observed between k_inh and redox potential.
  • Pluronic-silica nanoparticles (PluS-NO) exhibited a k_inh of 1.5 × 10^5 M^-1 s^-1.
  • Each PluS-NO particle, bearing approximately 30 nitroxide units, showed nearly double the inhibition duration of free nitroxides, resulting in an overall ~60-fold increase in inhibition.

Conclusions:

  • Pluronic-silica nanoparticles functionalized with nitroxides represent a promising strategy for developing advanced nanoantioxidants.
  • The covalent linkage and high density of nitroxide moieties on nanoparticles significantly enhance antioxidant duration and efficacy.
  • Further research should focus on optimizing linkage groups and understanding regeneration cycles for improved nanoantioxidant design.