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: 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
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.9K
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...
4.9K
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 Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.3K
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...
2.3K
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 Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.4K
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...
2.4K

You might also read

Related Articles

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

Sort by
Same author

Beyond electronic stabilization: towards a multicomponent conceptual density-functional theory for positron-driven bonding.

Physical chemistry chemical physics : PCCP·2026
Same author

Leveraging Chemical Hidden-Space Representations Effectively in Bayesian Optimization for Experiment Design through Dimension-Aware Hyperpriors.

Journal of chemical theory and computation·2026
Same author

Mild and Selective Oxidation of 4-Alkylpyridines to 4-Acylpyridines under an Oxygen Atmosphere.

The Journal of organic chemistry·2026
Same author

The Future of Foundation Machine Learning Potentials and DFT in Homogeneous Catalysis: Competition or Synergy?

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Implications from Geometric Phase for Circulating Far Away Conical Intersection(s).

The journal of physical chemistry. A·2026
Same author

A Cell-Resolved Ultrastable Biosensor Enables One-Step Detection of Gene-Fusion Transcripts in Unprocessed Whole Blood.

Angewandte Chemie (International ed. in English)·2026
Same journal

Synthetic Porous Carbons for High-Energy, High-Power Supercapacitors.

Chemical reviews·2026
Same journal

Navigating Misfolded Terrain: ER-Associated Degradation of Membrane Proteins.

Chemical reviews·2026
Same journal

Ink Design for Printing Perovskite Solar Cells and Modules.

Chemical reviews·2026
Same journal

Advanced Single-Atom Catalysts for Thermal-Catalytic C1 Chemistry.

Chemical reviews·2026
Same journal

Copper-Dependent Polysaccharide Monooxygenases: Mechanism and Function.

Chemical reviews·2026
Same journal

To Biotic or Abiotic: Biohybrid Systems for Artificial Photosynthesis.

Chemical reviews·2026
See all related articles

Related Experiment Video

Updated: Jan 6, 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

11.5K

Do Diradicals Behave Like Radicals?

Thijs Stuyver1, Bo Chen2, Tao Zeng3,4

  • 1Algemene Chemie , Vrije Universiteit Brussel , Pleinlaan 2 , 1050 Brussels , Belgium.

Chemical Reviews
|October 9, 2019
PubMed
Summary
This summary is machine-generated.

This review explores diradical reactivity, contrasting it with monoradicals by examining electronic structure and reaction pathways. Understanding diradical character is key to predicting their unique chemical behavior.

More Related Videos

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

11.2K
Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

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

Published on: April 15, 2013

20.7K

Related Experiment Videos

Last Updated: Jan 6, 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

11.5K
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

11.2K
Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

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

Published on: April 15, 2013

20.7K

Area of Science:

  • Physical Chemistry
  • Organic Chemistry
  • Quantum Chemistry

Background:

  • Diradicals possess two degenerate or nearly degenerate molecular orbitals occupied by two electrons.
  • Their electronic structure influences ground state spin and reactivity, differing significantly from monoradicals.

Purpose of the Study:

  • To delineate the electronic structure and reactivity of diradicals.
  • To compare diradical reactivity with monoradicals using prototypical radical reactions.
  • To critically survey measures of diradical character and their consequences.

Main Methods:

  • Analysis of electronic structure, including orbital transformations.
  • Computational examination of activation energies for dimerization, hydrogen abstraction, and addition reactions.
  • Comparative survey of diradical character measures.

Main Results:

  • Diradicals exhibit dual reactivity, influenced by delocalized-to-localized orbital transformations.
  • Activation energies for key reactions were calculated for diradicals and diradicaloids in different spin states.
  • Differences and similarities in reactivity between diradicals and monoradicals were elucidated.

Conclusions:

  • Diradical electronic structure and character are crucial for understanding their distinct reactivity.
  • Consistent theoretical levels reveal insights into diradical reaction mechanisms.
  • A comprehensive understanding of diradical character is essential for predicting their chemical behavior.