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: Steric Effects01:10

Radical Reactivity: Steric Effects

2.4K
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...
2.4K
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
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.6K
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...
2.6K
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 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: Abstraction00:47

Radical Formation: Abstraction

4.2K
The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...
4.2K

You might also read

Related Articles

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

Sort by
Same author

Homogeneous Copper(I) Electrocatalyzed Degradation of Ultra-Short and Long-Chain Perfluoroalkyl Substances.

ChemSusChem·2026
Same author

Alkene Hydrogenation by a Cationic, Nine-Coordinate Molybdenum(VI) Pentahydride Catalyst.

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

A low-spin manganese(II) complex with an emissive charge-transfer excited state.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Noninnocence Driven Superexchange Within a Ti<sup>2+</sup>/Ti<sup>4+</sup> Mixed Valence Complex.

Inorganic chemistry·2026
Same author

Combined Confocal Dynamic Light Scattering and Fluorescence Correlation Spectroscopy as an Advanced Technique to Characterize Colloidal Quantum Dot-Gold Nanoparticle Hybrid Systems.

Analytical chemistry·2026
Same author

Highly Acidic Second Coordination Spheres Promote In Situ Formation of Iron Phlorins Exhibiting Fast and Selective CO<sub>2</sub> Reduction.

Journal of the American Chemical Society·2026

Related Experiment Video

Updated: Jan 9, 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

N-centered, yet persistent: isolation of N2O-based radicals through FLP-type stabilization.

Andrea Orellana Ben Amor1, Laure Vendier1, Vincent César1

  • 1Univ. Toulouse, CNRS, LCC Toulouse France nicolas.queyriaux@lcc-toulouse.fr.

Chemical Science
|December 8, 2025
PubMed
Summary
This summary is machine-generated.

Stabilizing short-lived radical anions with Lewis acidic boranes creates persistent N-centered radicals. These novel species exhibit remarkable room-temperature stability, opening new avenues in radical chemistry.

More Related Videos

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
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

Related Experiment Videos

Last Updated: Jan 9, 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
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
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

Area of Science:

  • Organometallic Chemistry
  • Radical Chemistry
  • Boron Chemistry

Background:

  • The electrochemical reduction of N-heterocyclic carbenes (NHCs) like 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IDipp) typically yields unstable radical anions.
  • This instability limits their synthetic utility and detailed investigation.

Purpose of the Study:

  • To stabilize the electrochemically generated radical anion of IDipp·N2O.
  • To synthesize and characterize persistent radical species derived from NHCs.
  • To investigate the electronic structure and stability of these novel radicals.

Main Methods:

  • Electrochemical reduction of IDipp·N2O in the presence of Lewis acidic boranes.
  • Chemical reduction for synthesis of the stabilized radicals.
  • Electron paramagnetic resonance (EPR) spectroscopy (continuous-wave and pulsed).
  • Theoretical electronic structure calculations.

Main Results:

  • The one-electron reduction of IDipp·N2O, usually irreversible, becomes reversible upon stabilization with Lewis acidic boranes.
  • Persistent radical species are successfully synthesized and characterized.
  • These radicals exhibit a highly N-centered electronic structure.
  • Remarkable persistence at room temperature under inert atmosphere was observed.

Conclusions:

  • Lewis acidic boranes effectively stabilize transient NHC radical anions, transforming them into persistent radical species.
  • The stabilized radicals possess a unique N-centered character and significant room-temperature stability.
  • This work provides a new strategy for accessing and studying persistent NHC-based radicals.