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Preparation of Nitriles01:12

Preparation of Nitriles

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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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Nitrosation of Enols01:19

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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.
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Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

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The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic...
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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

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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.
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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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 bioinspired nitrone precursor to a stabilized nitroxide radical.

Amanda Capistrano Pinheiro1, Rodrigo Boni Fazzi1, Larissa Cerrato Esteves1

  • 1Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, 05508-000, São Paulo, SP, Brazil.

Free Radical Biology & Medicine
|April 2, 2021
PubMed
Summary

Researchers developed OxiBeet, a novel betalain-nitrone antioxidant. This biocompatible compound effectively scavenges radicals, outperforming common antioxidants and offering potential for new therapeutic strategies.

Keywords:
AntioxidantBetalainDelocalized radicalsEPRNitronesNitroxidePseudo-natural compounds

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Area of Science:

  • Natural product chemistry
  • Medicinal chemistry
  • Biochemistry

Background:

  • Nitrones from natural antioxidants show therapeutic promise for diseases like stroke, neurodegeneration, and cancer.
  • Betalains, natural pigments with antioxidant and pharmacological properties, are suitable precursors for designing multifunctional nitrones.

Purpose of the Study:

  • To describe the semisynthesis and properties of OxiBeet, a biocompatible and antioxidant betalain-nitrone.
  • To evaluate OxiBeet's radical scavenging capacity and compare it with established antioxidants.
  • To investigate the oxidation mechanism and resulting nitroxide radical of OxiBeet.

Main Methods:

  • Semisynthesis of the betalain-nitrone OxiBeet.
  • Radical scavenging assays comparing OxiBeet with ascorbic acid and gallic acid.
  • Electron paramagnetic resonance (EPR) spectroscopy to study the autoxidation product.
  • Femtosecond transient absorption spectroscopy to probe the oxidation mechanism.

Main Results:

  • OxiBeet demonstrated superior radical scavenging activity compared to ascorbic acid, gallic acid, and other non-phenolic antioxidants.
  • OxiBeet undergoes concerted proton-coupled electron transfer.
  • Autoxidation of OxiBeet yields a persistent nitroxide radical.
  • Excited state formation is not necessary for OxiBeet oxidation.

Conclusions:

  • OxiBeet is a potent, biocompatible antioxidant with potential therapeutic applications.
  • The study introduces a novel N-oxide 1,7-diazaheptamethinium scaffold for developing advanced antioxidant and spin-trap nitrones.
  • Betalain dyes can be engineered for enhanced stability in aqueous alkaline media, broadening their utility.