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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.2K
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...
2.2K
Radical Formation: Addition00:47

Radical Formation: Addition

1.8K
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...
1.8K
Radical Formation: Overview01:03

Radical Formation: Overview

2.2K
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...
2.2K
Radical Formation: Abstraction00:47

Radical Formation: Abstraction

3.7K
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...
3.7K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.0K
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...
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

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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Diradical Generation via Relayed Proton-Coupled Electron Transfer.

Qianqian Shi1, Zhipeng Pei2, Jinshuai Song1

  • 1Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou, Henan 450001, China.

Journal of the American Chemical Society
|February 8, 2022
PubMed
Summary
This summary is machine-generated.

A new relayed proton-coupled electron transfer (relayed-PCET) model explains diradical generation. This finding advances understanding of radical-radical cross-coupling reactions and opens new synthetic possibilities.

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Area of Science:

  • Organic Chemistry
  • Physical Chemistry
  • Reaction Mechanisms

Background:

  • Diradical generation followed by radical-radical cross-coupling is a key synthetic method.
  • The precise mechanism of diradical generation remains incompletely understood.

Purpose of the Study:

  • To propose and validate a novel mechanism for diradical generation.
  • To elucidate the electronic structural changes during radical processes.

Main Methods:

  • Quantum mechanics calculations were employed.
  • The study utilized a carbene-mediated diradical cross-coupling reaction model.
  • A specifically designed model was also investigated.

Main Results:

  • A new model, relayed proton-coupled electron transfer (relayed-PCET), was proposed and confirmed.
  • The detailed electronic structural changes during radical processes were observed.
  • The findings provide a new mechanistic insight into diradical generation.

Conclusions:

  • The confirmed relayed-PCET model offers a new perspective on diradical generation.
  • This mechanistic understanding could facilitate the development of novel radical-radical cross-coupling reactions.