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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.6K
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...
2.6K
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

2.1K
Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
2.1K
Radical Formation: Overview01:03

Radical Formation: Overview

2.6K
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...
2.6K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

4.2K
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.
4.2K
Radical Formation: Addition00:47

Radical Formation: Addition

2.1K
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...
2.1K
Radical Formation: Elimination00:51

Radical Formation: Elimination

2.2K
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...
2.2K

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Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
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Interfacial-Environment-Regulated Radical Pathways in Plasma-Induced C-X Bond Transformation.

Jun-Lei Yang1, Li-Hai Wei1, Peng Wu1,2

  • 1Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China.

ACS Applied Materials & Interfaces
|December 26, 2025
PubMed
Summary
This summary is machine-generated.

Interfacial environments control radical reactions on surfaces. Water promotes hydroxylation, while CO2/bicarbonate enable carboxylation of carbon-halogen bonds, guiding selective organic synthesis.

Keywords:
C−X bond transformationinterfacial environmentnanoscale resolutionradical reactiontip-enhanced Raman spectroscopy

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Area of Science:

  • Surface Chemistry
  • Organic Synthesis
  • Catalysis

Background:

  • Understanding radical-mediated carbon-halogen (C-X) bond activation is crucial for selective organic synthesis and sustainable conversion of halogenated compounds.
  • Interfacial environments significantly influence chemical transformations, but their role in radical pathways remains incompletely understood.

Purpose of the Study:

  • To elucidate the radical pathways governing C-X bond activation of 3-bromothiophenol on Au(111) under different interfacial environments.
  • To investigate how specific environmental factors, such as water and CO2, dictate reaction selectivity.

Main Methods:

  • Utilized helium low-temperature plasma as a controllable radical source.
  • Employed tip-enhanced Raman spectroscopy (TERS) for nanoscale visualization of reaction products and distributions.
  • Analyzed the impact of water, CO2, and bicarbonate on reaction pathways.

Main Results:

  • TERS imaging revealed distinct spatial distributions of coupling and hydroxylation products, indicating environment-dependent radical pathways.
  • Interfacial water was observed to steer the reaction from aryl-aryl coupling towards hydroxylation.
  • The presence of CO2 or bicarbonate redirected radical reactions towards selective carboxylation.

Conclusions:

  • Interfacial microenvironments fundamentally dictate the selectivity of radical-mediated C-X bond activation.
  • Demonstrated environmentally benign and controllable C-X bond activation processes.
  • Provided a mechanistic foundation for designing selective radical reactions based on interfacial conditions.