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Related Concept Videos

Radical Formation: Homolysis00:54

Radical Formation: Homolysis

4.6K
A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
4.6K
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

4.8K
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:
4.8K
Radical Formation: Abstraction00:47

Radical Formation: Abstraction

4.5K
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...
4.5K
Radical Formation: Overview01:03

Radical Formation: Overview

2.7K
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...
2.7K
Radical Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

4.7K
The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy...
4.7K
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

10.6K
In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
10.6K

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Related Experiment Video

Updated: Apr 15, 2026

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

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Organizing radical species in the solid state with halogen bonding.

Marc Fourmigué1, Julien Lieffrig

  • 1Institut des Sciences Chimiques de Rennes, Université Rennes 1 and CNRS, Campus de Beaulieu, 35042, Rennes, France, marc.fourmigue@univ-rennes1.fr.

Topics in Current Chemistry
|April 11, 2015
PubMed
Summary

The halogen bond effectively engineers solid-state radical systems for conductivity and magnetism. This review covers recent advances using halogen bonds in radical donors, acceptors, and charge transfer salts.

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
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Area of Science:

  • Solid-state chemistry
  • Materials science
  • Supramolecular chemistry

Background:

  • Electronic properties of radical systems depend on spin delocalization and intermolecular interactions.
  • Halogen bonding is a key interaction for engineering magnetic and conducting materials.

Purpose of the Study:

  • To review recent advances in using halogen bonds to engineer electronic properties of radical systems.
  • To discuss three distinct scenarios involving halogen bonds and radical species.

Main Methods:

  • Review of existing literature on halogen bonding in radical systems.
  • Analysis of molecular structures and electronic properties.
  • Categorization of systems based on the role of radical species in halogen bonding.

Main Results:

  • Halogenated radical species can act as effective halogen bond donors.
  • Radical species can also function as halogen bond acceptors.
  • Charge transfer salts can be designed where both donor and acceptor are radical species.

Conclusions:

  • Halogen bonding is a versatile tool for controlling electronic properties in radical-based materials.
  • The ability to tune molecular interactions via halogen bonds opens new avenues for designing advanced functional materials.