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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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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

11.2K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
11.2K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.3K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
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Electron Paramagnetic Resonance (EPR) Spectroscopy: Organic Radicals01:17

Electron Paramagnetic Resonance (EPR) Spectroscopy: Organic Radicals

3.6K
Ideally, an unpaired electron shows a single peak in the EPR spectrum due to the transition between the two spin energy states. However, coupling interactions can occur between the spins of the unpaired electron and any neighboring spin-active nuclei. This hyperfine coupling results in hyperfine splitting, where the EPR signal is split into multiplets. The signals split into 2nI + 1 peaks, where n is the number of equivalent nuclei and I is the nuclear spin. These splitting patterns provide...
3.6K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.5K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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Detection of Nitric Oxide and Superoxide Radical Anion by Electron Paramagnetic Resonance Spectroscopy from Cells using Spin Traps
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Triarylmethyl-based biradical as a superoxide probe.

Martin Poncelet1,2, Benoit Driesschaert1,2, Andrey A Bobko1,2

  • 1a In Vivo Multifunctional Magnetic Resonance center, Robert C. Byrd Health Sciences Center, West Virginia University , Morgantown , WV , USA.

Free Radical Research
|August 19, 2017
PubMed
Summary

Researchers synthesized a novel triarylmethyl (TAM) biradical for precise superoxide radical detection. This method utilizes electron paramagnetic resonance (EPR) for sensitive and selective superoxide measurements in biological systems.

Keywords:
AtropoisomerismEPRbiradicalreactive oxygen species (ROS)superoxidetrityl

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Use of Electron Paramagnetic Resonance in Biological Samples at Ambient Temperature and 77 K
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Detection of Nitric Oxide and Superoxide Radical Anion by Electron Paramagnetic Resonance Spectroscopy from Cells using Spin Traps
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Rapid Scan Electron Paramagnetic Resonance Opens New Avenues for Imaging Physiologically Important Parameters In Vivo
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Area of Science:

  • Biochemistry
  • Chemical Biology
  • Spectroscopy

Background:

  • Superoxide radicals are key reactive oxygen species in biological processes.
  • Electron paramagnetic resonance (EPR) using triarylmethyl (TAM) radicals offers selective superoxide detection.
  • Existing methods require optimization for sensitivity and reaction kinetics.

Purpose of the Study:

  • To develop a novel TAM-TAM biradical for enhanced superoxide measurement.
  • To characterize the reactivity and kinetics of the new biradical with superoxide.
  • To establish a sensitive EPR-based assay for superoxide quantification.

Main Methods:

  • Straightforward synthesis of a TAM-TAM biradical.
  • Characterization of the biradical using EPR spectroscopy.
  • Kinetic analysis of the reaction between the biradical and superoxide radicals.

Main Results:

  • A novel TAM-TAM biradical was successfully synthesized and characterized.
  • The biradical exhibits high reactivity towards superoxide radicals.
  • A second-order rate constant of (6.7 ± 0.2) × 10^3 M^-1 s^-1 was determined for the reaction.
  • The method allows superoxide measurement via an increased EPR signal from the product.

Conclusions:

  • The developed TAM-TAM biradical provides a sensitive and selective tool for superoxide measurement.
  • This EPR-based approach offers advantages in studying biological processes involving superoxide.
  • The straightforward synthesis and high reactivity facilitate broader applications in oxidative stress research.