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Related Concept Videos

Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.1K
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
4.1K
Radical Formation: Overview01:03

Radical Formation: Overview

2.1K
A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
2.1K
Radical Formation: Addition00:47

Radical Formation: Addition

1.7K
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...
1.7K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
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...
2.1K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

1.9K
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...
1.9K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

3.6K
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.
3.6K

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Related Experiment Video

Updated: Jul 26, 2025

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow
10:34

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow

Published on: April 24, 2014

10.8K

Radical approaches to C-S bonds.

Zijun Wu1, Derek A Pratt2

  • 1Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, Ontario, Canada.

Nature Reviews. Chemistry
|June 21, 2023
PubMed
Summary

Radical chemistry offers new ways to create organosulfur compounds, essential in medicine and materials. These methods allow for late-stage functionalization, simplifying complex molecule synthesis.

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene
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Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene

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Related Experiment Videos

Last Updated: Jul 26, 2025

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow
10:34

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow

Published on: April 24, 2014

10.8K
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

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Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene
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Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in PolyS-Divinylbenzene

Published on: May 20, 2019

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Materials Science

Background:

  • Organosulfur compounds are vital in pharmaceuticals, agrochemicals, and materials.
  • Traditional synthesis relies on ionic chemistry, often requiring lengthy procedures.
  • Recent advances highlight radical-based methods for installing sulfur functionalities.

Purpose of the Study:

  • To review homolytic carbon-sulfur bond-forming processes.
  • To emphasize radical substitution for sulfides, disulfides, and sulfinyls.
  • To discuss sulfur dioxide and surrogates for sulfonyl synthesis.

Main Methods:

  • Focus on radical substitution reactions.
  • Utilize sulfur dioxide and its surrogates.
  • Analyze mechanistic aspects of C-S bond formation.

Main Results:

  • Radical methods enable late-stage functionalization of complex molecules.
  • Avoids the need for protecting labile organosulfur groups.
  • Provides efficient routes to various organosulfur compounds.

Conclusions:

  • Radical-based strategies offer powerful alternatives to ionic methods.
  • Mechanistic understanding is key to developing new synthetic routes.
  • These methods are compatible with diverse organosulfur moieties in modern chemistry.