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Related Concept Videos

Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Radical Autoxidation01:20

Radical Autoxidation

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...
Radical Formation: Elimination00:51

Radical Formation: Elimination

Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect to...
Radical Chain-Growth Polymerization: Overview01:10

Radical Chain-Growth Polymerization: Overview

Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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Radical Reactivity: Overview

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 molecule. These three...
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Oxidation and Reduction of Organic Molecules

Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
The removal of an electron from a molecule, results in a...

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Related Experiment Video

Updated: Jun 28, 2026

Enabling Real-Time Compensation in Fast Photochemical Oxidations of Proteins for the Determination of Protein Topography Changes
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Published on: September 1, 2020

A new kinetic method for quantification phenoxyl free radicals.

Jing Xu1, Xinguo Wu, Wei Yan

  • 1College of Chemistry and Molecular Science, Wuhan University, Wuhan, 430072, PR China.

Talanta
|October 31, 2008
PubMed
Summary

A new kinetic method quantifies phenoxyl radicals using reduced nicotinamide adenine dinucleotide (NADH) as a probe. This sensitive technique measures radical reactivity, aiding environmental monitoring of chlorophenol oxidation.

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Area of Science:

  • Analytical Chemistry
  • Environmental Chemistry
  • Biochemistry

Background:

  • Phenoxyl radicals are key intermediates in enzymatic oxidation reactions.
  • Direct detection of phenoxyl radicals is challenging due to their transient nature.
  • Quantifying these radicals is crucial for understanding environmental pollutant degradation.

Purpose of the Study:

  • To develop a novel kinetic method for quantifying phenoxyl radicals.
  • To utilize reduced nicotinamide adenine dinucleotide (NADH) as a sensitive probe for phenoxyl radical formation.
  • To investigate the reactivity of various chlorophenol-derived phenoxyl radicals.

Main Methods:

  • Employed stopped-flow fast scanning spectrophotometry to monitor rapid NADH oxidation.
  • Correlated the initial rate of NADH oxidation to phenoxyl radical concentration.
  • Investigated phenoxyl radicals generated from 2-CP, 4-CP, 2,4-DCP, 2,4,6-TCP, and 2,3,4,6-Tetra-CP using horseradish peroxidase and hydrogen peroxide.

Main Results:

  • The method demonstrated high sensitivity, detecting phenoxyl radicals from 1x10(-8)M 2,4-DCP.
  • Established the reactivity order of phenoxyl radicals: 2,4-DCP > 4-CP > 2-CP > 2,4,6-TCP > 2,3,4,6-Tetra-CP.
  • Confirmed the method's feasibility for determining enzymatic phenoxyl radical generation in lake water samples.

Conclusions:

  • The proposed kinetic method offers a sensitive and reliable approach for phenoxyl radical quantification.
  • The study provides insights into the reactivity of different chlorophenol-derived radicals.
  • This method has practical applications in environmental analysis and monitoring.