Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For instance, consider...
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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 low‐energy SOMO, which interacts...
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 Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
Radical Formation: Addition00:47

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 unpaired...
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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 carbon–halogen...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Exploiting Pnictogen σ/π-Hole Interactions for Visible-Light-Induced Radical Transformations.

Accounts of chemical research·2026
Same author

Green-Light-Induced Cyclopropanation of Alkenes via Cooperative NHN/Ligated Boryl Radical Activation of Dichloromethane.

Organic letters·2026
Same author

Harnessing Pnictogen and Chalcogen Bonding for Cross-Electrophile C-P<sup>III</sup> Coupling of Chlorophosphines with Thianthrenium Salts.

Organic letters·2025
Same author

Direct Boron-10 Access: Nickel-Catalyzed Reductive C(sp<sup>2</sup>)─<sup>10</sup>B Coupling Utilizing <sup>10</sup>BF<sub>3</sub>.

Angewandte Chemie (International ed. in English)·2025
Same author

Near-Infrared-Light-Induced Iron(I) Dimer Enabled Abstraction of Ester Group from Cycloketone Oxime Esters.

Organic letters·2025
Same author

N-heterocyclic nitrenium-catalyzed photosynthesis of 3,3-disubstituted oxindoles from α-chloroanilides.

Organic & biomolecular chemistry·2024
Same journal

An intrinsically stretchable nanowire-based sensing patch for wearable analysis of sweat chloride ion composition.

Chemical communications (Cambridge, England)·2026
Same journal

A sterically rigid-flexible balanced NHC-Pd precatalyst for room-temperature solvent-free C-N coupling of benzocyclic amines.

Chemical communications (Cambridge, England)·2026
Same journal

Portable fluorescent conjugated microporous polymer sensor coupled with a smartphone for on-site Fe<sup>3+</sup> detection in water.

Chemical communications (Cambridge, England)·2026
Same journal

Accelerated discovery of NO<sub>3</sub>RR single-atom catalysts <i>via</i> high-throughput DFT and machine learning.

Chemical communications (Cambridge, England)·2026
Same journal

Wafer-scale robust graphene electronics under industrial processing conditions.

Chemical communications (Cambridge, England)·2026
Same journal

Subnanoscale IrW oxide anodes: breaking immiscibility for high activity and durability in water electrolysis.

Chemical communications (Cambridge, England)·2026
See all related articles

Related Experiment Video

Updated: Jun 17, 2026

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

Chalcogen σ-hole interaction enabled radical reactions.

Yan Zhang1, Jin-Ru Chen1, Xiang-Yu Chen2,3

  • 1School of Chemistry and Chemical Engineering, Shandong University of Technology, 266 West Xincun Road, Zibo 255049, China. qiangliu@sdut.edu.cn.

Chemical Communications (Cambridge, England)
|June 16, 2026
PubMed
Summary
This summary is machine-generated.

Chalcogen bonding (ChB) activates chemical reactions via σ-hole interactions. This review explores ChB-enabled radical reactions, showcasing mild, metal-free conditions for novel synthetic pathways.

More Related Videos

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of Chalcogenidoplumbates(II or IV)
10:42

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of Chalcogenidoplumbates(II or IV)

Published on: December 29, 2016

Related Experiment Videos

Last Updated: Jun 17, 2026

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

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of Chalcogenidoplumbates(II or IV)
10:42

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of Chalcogenidoplumbates(II or IV)

Published on: December 29, 2016

Area of Science:

  • Chemistry
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Chalcogen bonding (ChB) is a noncovalent interaction involving Group 16 elements.
  • ChB has emerged as a significant activation strategy in synthetic chemistry.
  • Radical reactions are fundamental in organic synthesis.

Purpose of the Study:

  • To provide a comprehensive overview of Chalcogen bonding-enabled radical reactions.
  • To highlight the use of ChB interactions for unprecedented reactivity under mild conditions.
  • To explore mechanistic themes in ChB-driven radical chemistry.

Main Methods:

  • Review of existing literature on Chalcogen bonding and radical reactions.
  • Categorization of ChB-enabled radical reactions into cationic and neutral mechanisms.
  • Analysis of mechanistic insights from spectroscopic, computational, and radical-trapping studies.

Main Results:

  • ChB interactions facilitate radical generation under mild, transition metal-free, and photocatalyst-free conditions.
  • Cationic ChB involves sulfonium and selenonium salts forming photoactive complexes.
  • Neutral ChB plays a critical role in orchestrating single-electron transfer processes.

Conclusions:

  • Chalcogen bonding offers a tunable and versatile platform for radical generation.
  • ChB-enabled radical reactions unlock novel synthetic possibilities.
  • Future applications include asymmetric catalysis, multicatalytic networks, and continuous-flow synthesis.