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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 Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

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 factors, steric factors also account...
Radical Reactivity: Overview01:11

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...
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...
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.

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Updated: May 23, 2026

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry
12:11

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry

Published on: April 8, 2020

The phenoxyl radical-water complex--a matrix isolation and computational study.

Wolfram Sander1, Saonli Roy, Iakov Polyak

  • 1Lehrstuhl für Organische Chemie II, Ruhr-Universität Bochum, D-44801 Bochum, Germany. wolfram.sander@rub.de

Journal of the American Chemical Society
|April 10, 2012
PubMed
Summary

Researchers generated the phenoxyl radical and studied its interaction with water in argon matrices. They identified an OH···O complex, offering insights into biological systems like the tyrosyl radical interaction with water.

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Last Updated: May 23, 2026

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry
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Area of Science:

  • Physical Chemistry
  • Spectroscopy
  • Computational Chemistry

Background:

  • Phenoxyl radicals are key intermediates in various chemical reactions.
  • Understanding radical-water interactions is crucial for biological processes.

Purpose of the Study:

  • To characterize the interaction between the phenoxyl radical and water.
  • To investigate the stability of radical-water complexes in low-temperature matrices.

Main Methods:

  • Flash vacuum pyrolysis of allyl phenyl ether to generate the phenoxyl radical.
  • Trapping products in argon matrices at 3 K.
  • Infrared (IR) spectroscopy for complex characterization.
  • Density functional theory (DFT) and QM/MM calculations.

Main Results:

  • High yields of the phenoxyl radical were achieved.
  • An OH···O complex between the phenoxyl radical and water was identified and characterized by IR spectroscopy.
  • Isotopomers confirmed the complex structure.
  • No other dimers were observed under experimental conditions.
  • QM/MM calculations indicated instability of OH···π complexes.

Conclusions:

  • The OH···O complex is the primary interaction product between the phenoxyl radical and water in argon matrices.
  • The findings suggest specific binding modes relevant to biological systems.
  • The instability of OH···π complexes has implications for understanding tyrosyl radical-water interactions in proteins.