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

3.0K
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...
3.0K
Energy Diagrams, Transition States, and Intermediates02:13

Energy Diagrams, Transition States, and Intermediates

22.0K
Free-energy diagrams, or reaction coordinate diagrams, are graphs showing the energy changes that occur during a chemical reaction. The reaction coordinate represented on the horizontal axis shows how far the reaction has progressed structurally. Positions along the x-axis close to the reactants have structures resembling the reactants, while positions close to the products resemble the products.  Peaks on the energy diagram represent stable structures with measurable lifetimes, while...
22.0K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

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

Radical Reactivity: Intramolecular vs Intermolecular

2.3K
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...
2.3K
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

5.3K
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...
5.3K
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

4.7K
Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
4.7K

You might also read

Related Articles

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

Sort by
Same author

Reinvestigation of the mechanism and selectivity of 1,8-cineole synthase using <i>TerDockin</i>.

Chemical science·2026
Same author

The One Ring: A Monocycle Producing Class II Diterpene Cyclase from <i>Isodon leucophyllus</i>.

Journal of the American Chemical Society·2026
Same author

Investigations toward a unified reaction pathway of thermal and TBSOTf-mediated oxidopyrylium-alkene (5 + 2) cycloadditions.

Organic & biomolecular chemistry·2026
Same author

Enantioselective Synthesis of Complex Carbocycles by C-H Insertion of Aryl/Aryl Carbenes.

ACS catalysis·2026
Same author

Ab Initio Molecular Dynamics Simulations for Organic Chemists─It is About Time!

Journal of the American Chemical Society·2026
Same author

Dock & design: engineering specificity for an alternative pimaradiene outcome with the <i>ent</i>-kaurene synthase from <i>Bradyrhizobium japonicum</i>.

Chemical science·2026
Same journal

Selective Synthesis of 2-Substituted Quinolines via Amine-Assisted Heck Reaction of 2-Iodoanilines with α,β-Unsaturated Aldehydes.

The Journal of organic chemistry·2026
Same journal

Asymmetric Total Synthesis of Naturally Occurring (-)-EBC-329 through an (<i>E</i>)-Selective Cross-Metathesis Reaction.

The Journal of organic chemistry·2026
Same journal

Ruthenium(II)-Catalyzed [2 + 1 + 3] Annulation of 3-Aryl-3-hydroxyisoindolinones with Diazopyrazolones: Step-Economical Synthesis of Spiro[1,3-oxazine-pyrazolones].

The Journal of organic chemistry·2026
Same journal

Electrochemical Cascade Cyclization of Sulfoxonium Ylides with Unactivated Alkenes.

The Journal of organic chemistry·2026
Same journal

How Hexafluoroisopropanol Catalyzes the Michael Addition of Anilines to Maleimides: Mechanistic Insights from Density Functional Theory and Classical Force-Field Molecular Dynamics.

The Journal of organic chemistry·2026
Same journal

Copper-Catalyzed Intermolecular Carbosulfonylation of Alkynes to Access Functionalized Eight-Membered Tetrahydroazocines.

The Journal of organic chemistry·2026
See all related articles

Related Experiment Video

Updated: Mar 20, 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

11.8K

When To Let Go-Diradical Intermediates from Zwitterionic Transition State Structures?

Q Nhu N Nguyen1, Dean J Tantillo1

  • 1Department of Chemistry, University of California-Davis , Davis, California 95616, United States.

The Journal of Organic Chemistry
|May 27, 2016
PubMed
Summary
This summary is machine-generated.

Density functional theory calculations reveal that Brummond-Chen thermal intramolecular (2+2)-cycloaddition reactions may involve diradical intermediates. The formation of these intermediates is influenced by substituent type and solvent polarity.

More Related Videos

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

3.4K
Thermochemical Studies of NiII and ZnII Ternary Complexes Using Ion Mobility-Mass Spectrometry
16:11

Thermochemical Studies of NiII and ZnII Ternary Complexes Using Ion Mobility-Mass Spectrometry

Published on: June 8, 2022

2.8K

Related Experiment Videos

Last Updated: Mar 20, 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

11.8K
Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

3.4K
Thermochemical Studies of NiII and ZnII Ternary Complexes Using Ion Mobility-Mass Spectrometry
16:11

Thermochemical Studies of NiII and ZnII Ternary Complexes Using Ion Mobility-Mass Spectrometry

Published on: June 8, 2022

2.8K

Area of Science:

  • Organic Chemistry
  • Computational Chemistry

Background:

  • Brummond-Chen reactions are a class of thermal intramolecular (2+2)-cycloadditions.
  • Understanding reaction mechanisms is crucial for synthetic chemistry.

Purpose of the Study:

  • To investigate the mechanistic pathways of Brummond-Chen thermal intramolecular (2+2)-cycloaddition reactions.
  • To explore the potential role of diradical intermediates in these reactions.

Main Methods:

  • Utilized density functional theory (DFT) calculations.
  • Analyzed reaction pathways and transition states.

Main Results:

  • DFT calculations suggest diradical intermediates can form directly from zwitterionic transition states.
  • The probability of diradical intermediate formation is sensitive to substituent effects.
  • Solvent polarity significantly impacts the likelihood of diradical intermediate involvement.

Conclusions:

  • The mechanism of Brummond-Chen reactions can involve diradical intermediates.
  • Reaction outcomes are tunable through careful selection of substituents and solvents.