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

2.0K
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...
2.0K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.2K
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...
2.2K
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

3.8K
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:
3.8K
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.1K
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...
4.1K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.9K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
1.9K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.2K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.2K

You might also read

Related Articles

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

Sort by
Same author

O<sub>2</sub> Activation at an Enzymatic Diiron Site: Bridging Ligand Substitutions Alter Diferric-(Hydro)peroxo States.

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

A Series of Trigonal Arylimido Iron Complexes and the Influence of Oxidation State and Steric Demand on Reactivity.

Inorganic chemistry·2025
Same author

The flexible behaviour of a trigonal arylimido iron complex.

Chemical communications (Cambridge, England)·2025
Same author

Linear open-shell 3d-metal silylamides - a versatile tool in coordination chemistry.

Chemical communications (Cambridge, England)·2025
Same author

Promiscuity in Molecular Mimics of the Cysteine Dioxygenase: Effects of Selenium in the Substrate and Cobalt as the Central Metal Ion.

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

FeNb<sub>2</sub>O<sub>6</sub> as a High-Performance Anode for Sodium-Ion Batteries Enabled by Structural Amorphization Coupled with NbO<sub>6</sub> Local Ordering.

Advanced materials (Deerfield Beach, Fla.)·2025

Related Experiment Video

Updated: Aug 16, 2025

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
10:21

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions

Published on: October 5, 2019

8.5K

Taming the stilbene radical anion.

Grégoire Sieg1, Igor Müller1, Kilian Weißer2

  • 1Fachbereich Chemie, Philipps-Universität Marburg Hans-Meerwein-Straße 4 35037 Marburg Germany gunnar.werncke@chemie.uni-marburg.de.

Chemical Science
|December 22, 2022
PubMed
Summary

Researchers isolated and characterized the first simple alkene radical anion, stilbene, using potassium cations. This breakthrough enables new catalytic applications for organic electron conductors and facilitates Z to E isomerization.

More Related Videos

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

10.9K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

2.8K

Related Experiment Videos

Last Updated: Aug 16, 2025

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
10:21

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions

Published on: October 5, 2019

8.5K
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

10.9K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

2.8K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Materials Science

Background:

  • Organic radical anions are key intermediates in reductions and have potential in catalysis and conductive materials.
  • Typically, only extended aromatic systems allow isolation; simple unsaturated hydrocarbons are observed transiently.
  • The instability of non-aromatic radical anions limits their study and application.

Purpose of the Study:

  • To report the first isolation, structure, and characterization of a simple aryl-substituted alkene radical anion.
  • To investigate the role of radical anions in Z → E isomerization of alkenes.
  • To explore the use of iron complexes as reductants for generating and stabilizing radical anions.

Main Methods:

  • Encapsulation of stilbene radical anion between two potassium (18-crown-6) cations.
  • Spectroscopic characterization (e.g., EPR, NMR) of the isolated radical anion.
  • Utilizing a linear iron(I) complex as a reductant and coordination site.

Main Results:

  • Successful isolation and structural determination of the stilbene radical anion.
  • Observed Z → E isomerization of the alkene double bond upon radical anion formation, even on a catalytic scale.
  • Demonstrated that an iron(I) complex can act as a reductant to form an iron(II)-bound radical anion, enabling isomerization of various alkenes.

Conclusions:

  • The first stable, simple alkene radical anion (stilbene) has been isolated and characterized.
  • Radical anion formation is linked to catalytic Z → E isomerization of alkenes.
  • Iron complexes offer a versatile route for generating radical anions and driving alkene isomerization, expanding their synthetic utility.