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Related Concept Videos

Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

5.4K
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...
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π Molecular Orbitals of the Allyl Radical01:27

π Molecular Orbitals of the Allyl Radical

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Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
The allyl systems have identical molecular orbitals but differ in the number of π electrons....
4.8K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.6K
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...
2.6K
Radical Formation: Addition00:47

Radical Formation: Addition

2.4K
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...
2.4K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.6K
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...
2.6K
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...
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Related Experiment Video

Updated: Mar 28, 2026

Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow
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Exploring the Radical Nature of a Carbon Surface by Electron Paramagnetic Resonance and a Calibrated Gas Flow

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Air- and Water-Persistent C‑Centered Radical Anion Based on FLP-Type-Activated CO2.

Caroline Gonçalves1, Agustín Morales1,2, Léon Escomel1

  • 1Université de Toulouse, LCC-CNRS, 205 Route de Narbonne, 31077 Toulouse Cedex 04, France.

JACS Au
|March 27, 2026
PubMed
Summary

Researchers created the first stable radical anion from carbon dioxide (CO2). This breakthrough advances the study and application of persistent organic radicals, which are crucial in various scientific fields.

Keywords:
CO2FLP-type activationair-persistent radicalradical anionthrough-space radical delocalization

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Last Updated: Mar 28, 2026

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Area of Science:

  • Chemistry
  • Materials Science
  • Biochemistry

Background:

  • Organic radicals are essential in chemistry, biology, and materials science.
  • Stabilizing highly reactive open-shell molecules is key to understanding their properties and applications.
  • Air-persistent organic radicals (APORs) represent a significant advancement in radical stability.

Purpose of the Study:

  • To report the first air- and water-persistent radical anion derived from carbon dioxide (CO2).
  • To investigate the stabilization mechanisms of this novel CO2 radical anion.

Main Methods:

  • Generation of the CO2 radical anion from an FLP-type-activated CO2 adduct.
  • Utilizing an N-heterocyclic carbene (NHC) as the Lewis base.
  • Employing a ditopic perfluorinated diborane as the Lewis acid.
  • Conducting combined experimental and theoretical studies.

Main Results:

  • Successfully synthesized the first air- and water-persistent radical anion of CO2.
  • The radical anion is derived from a CO2 adduct stabilized by an NHC and a perfluorinated diborane.
  • Both thermodynamic and kinetic factors contribute to the observed stability.

Conclusions:

  • The development of persistent CO2 radical anions opens new avenues in radical chemistry.
  • This work provides a benchmark for the stability of open-shell species derived from small molecules.
  • Further research into FLP-activated systems can lead to novel stable radical species.