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Radical Reactivity: Overview

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...

Radical Reactivity: Steric Effects

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...

Radical Autoxidation

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 Chain-Growth Polymerization: Mechanism

Radical Chain-Growth Polymerization: Mechanism

The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this...

Radical Formation: Addition

Radical Formation: Addition

Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...

Radical Reactivity: Concentration Effects

Radical Reactivity: Concentration Effects

In a radical reaction, the concentration of starting materials governs the selectivity of a radical. For example, the reaction between an alkyl halide and an alkene, in the presence of tin hydride and AIBN, begins with the generation of a tin radical. The generated radical then abstracts halogen from the alkyl halide, producing an alkyl radical. This alkyl radical can either react with tin hydride, yielding an alkane, or add to an alkene, generating a nitrile-stabilized radical, eventually...

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Updated: Jun 15, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

Productive chemistry induced by mechanochemically generated macroradicals.

Chenxu Wang^1,2, Cai-Li Sun¹, Roman Boulatov²

¹College of Chemistry and Chemical Engineering, Xi'an University of Science and Technology, Xi'an 710054, China. chenxuwang@xust.edu.cn.

Chemical Communications (Cambridge, England)

|August 22, 2024

Summary

Polymer mechanochemistry can now harness chain-breaking radicals to self-heal or self-strengthen materials. This approach offers new insights into material failure and load distribution under mechanical stress.

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Last Updated: Jun 15, 2025

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Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

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Published on: April 15, 2013

Area of Science:

Polymer Science
Materials Chemistry
Mechanochemistry

Background:

Mechanical loads degrade polymers via chain fragmentation, forming reactive macroradicals.
Existing strategies focus on dissipating strain to prevent fracture.
Macroradicals initiate damaging reaction cascades.

Purpose of the Study:

Summarize a complementary strategy in polymer mechanochemistry.
Explore channeling macroradicals for material self-healing or self-strengthening.
Investigate using mechanofluorescence for understanding load distribution.

Main Methods:

Review of emerging strategies in polymer mechanochemistry.
Analysis of radical channeling for bond formation and fluorescence.
Identification of generalizable lessons and challenges.

Main Results:

Mechanochemically generated macroradicals can form new load-bearing bonds.
This process enables local self-healing and self-strengthening.
Mechanofluorescence can provide quantitative insights into mechanical load distribution.

Conclusions:

Channelling macroradicals is a promising complementary strategy to suppress polymer degradation.
This approach offers pathways for self-healing, self-strengthening, and advanced material characterization.
Key challenges remain in adapting this strategy to diverse materials and loading conditions.