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

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

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...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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...

You might also read

Related Articles

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

Sort by
Same author

New sesquiterpene lactones and other constituents from Ammodaucus leucotrichus growing wild in Algeria.

Fitoterapia·2026
Same author

Controlled Triazine-Based Covalent Functionalization of Black Phosphorus for Degradable Hybrid Materials.

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

Interface Stability and Kinetics of Sulfide Electrolytes in all-Solid-State Batteries.

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

Electron-Deficient Phenazines: Synthesis, Structures, Redox, and Optoelectronic Properties in the Gas Phase, in Solution, and in the Solid State.

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

The role of nickel hydroxide phases in wastewater electrolysis for sustainable green hydrogen production.

Nanoscale·2026
Same author

Driving forward the restoration of an American icon.

Science (New York, N.Y.)·2026

Related Experiment Video

Updated: May 23, 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

Halogenated benzene cation radicals.

Matthias J Molski1, Doreen Mollenhauer, Sebastian Gohr

  • 1Freie Universität Berlin, Institut für Chemie und Biochemie, Fabeckstrasse 34-36, 14195 Berlin, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 11, 2012
PubMed
Summary
This summary is machine-generated.

Researchers studied halogenated benzene cation radicals, finding thermal stability increases with less hydrogen. Some cation radicals showed geometric distortions, while others maintained symmetry, explained by DFT calculations.

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

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Related Experiment Videos

Last Updated: May 23, 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

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Area of Science:

  • Inorganic Chemistry
  • Physical Chemistry
  • Materials Science

Background:

  • Halogenated benzenes are versatile chemical building blocks.
  • Understanding the electronic and structural properties of their cation radicals is crucial for developing new materials and chemical processes.
  • Previous studies have explored the reactivity of these compounds, but detailed structural characterization of their cation radicals remains an active area of research.

Purpose of the Study:

  • To synthesize and characterize cation radicals of various halogenated benzenes.
  • To investigate the structural changes and thermal stability of these cation radicals.
  • To elucidate the factors influencing geometric distortions, particularly Jahn-Teller distortions, using computational methods.

Main Methods:

  • Oxidation of halogenated benzenes using strong oxidants to form cation radicals.
  • Isolation and characterization of cation-radical salts.
  • Electron paramagnetic resonance (EPR) spectroscopy and single-crystal X-ray diffraction for structural analysis.
  • Density Functional Theory (DFT) calculations to explain observed geometries.

Main Results:

  • Cation radicals were successfully isolated and characterized.
  • Thermal stability increased with decreasing hydrogen content in the halogenated benzene precursors.
  • Jahn-Teller distortions were observed in perfluorinated and perchlorinated benzene cation radicals, with some exhibiting multiple low-symmetry geometries.
  • Cation radicals of 2,4,6-trifluorobenzene and hexaiodobenzene did not show Jahn-Teller distortions, with DFT calculations providing distinct explanations for each.

Conclusions:

  • The hydrogen content significantly influences the thermal stability of halogenated benzene cation radicals.
  • Jahn-Teller distortions are prevalent in highly fluorinated and chlorinated benzene cation radicals, but not universally observed in all halogenated analogs.
  • DFT calculations are essential for understanding the nuanced electronic and structural behaviors of these cation radicals and predicting their geometries.