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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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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...
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Radical Formation: Addition00:47

Radical Formation: Addition

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Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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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...
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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: 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 Formation: Homolysis00:54

Radical Formation: Homolysis

4.2K
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.
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Reversible Interconversion between a Carbon-Carbon Double Bond and Diradical beyond External Stimulus.

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Researchers developed a new method using Lewis acids to twist carbon-carbon double bonds into stable diradical species. This reversible process opens doors for novel molecular design and responsive materials.

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Area of Science:

  • Organic Chemistry
  • Materials Science

Background:

  • Reversible interconversion between carbon-carbon double bonds and diradical species is a key challenge.
  • Achieving stable diradical states via controlled bond twisting is difficult.

Purpose of the Study:

  • To develop a strategy for controlled twisting of C═C bonds into diradical species.
  • To explore the reversibility of this transformation.

Main Methods:

  • Lewis acid coordination (Al(ORF)3 or SiEt3+) to bianthrone derivatives.
  • Characterization using X-ray crystallography, EPR spectroscopy, and magnetic studies.
  • Monitoring reversibility with UV-vis and NMR spectroscopy.

Main Results:

  • Achieved controlled twisting of C═C bonds to over 70° using Lewis acids.
  • Isolated and characterized stable twisted diradical adducts.
  • Demonstrated reversible conversion back to folded alkenes upon Lewis acid displacement.

Conclusions:

  • Lewis acid coordination provides a method to manipulate C═C bond topology and form diradicals.
  • The diradical formation is reversible, enabling responsive molecular systems.
  • Potential applications in molecular design and electronic materials.