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Related Concept Videos

Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

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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...
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Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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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...
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Radical Formation: Homolysis00:54

Radical Formation: Homolysis

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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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Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

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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.
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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.5K
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: Abstraction00:47

Radical Formation: Abstraction

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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.
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Related Experiment Video

Updated: Dec 9, 2025

Measurement of Ultrafast Vibrational Coherences in Polyatomic Radical Cations with Strong-Field Adiabatic Ionization
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A Room-Temperature Stable Distonic Radical Cation.

Xiaodan Chen1, Liu Leo Liu2, Shihua Liu3,4

  • 1College of Chemistry and Materials Science, Jinan University, Guangzhou, 510632, China.

Angewandte Chemie (International Ed. in English)
|September 11, 2020
PubMed
Summary

Researchers isolated a stable, crystalline dicarbondiphosphide-based β-distonic radical cation salt at room temperature. This phosphorus radical cation is the closest isolable entity to a genuine distonic radical cation (DRC) to date.

Keywords:
carbenesdicarbondiphosphidedistonic radical cationsphosphorusradicals

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Area of Science:

  • Inorganic Chemistry
  • Radical Chemistry
  • Organophosphorus Chemistry

Background:

  • Distonic radical cations (DRCs) with spatially separated charge and radical sites are typically observed in gas-phase mass spectrometry or matrix isolation spectroscopy.
  • The isolation of stable DRCs in the solid state remains a significant challenge in chemistry.

Purpose of the Study:

  • To report the isolation and characterization of a novel crystalline dicarbondiphosphide-based β-distonic radical cation salt.
  • To investigate the electronic structure and properties of this unique phosphorus radical cation species.

Main Methods:

  • One-electron oxidation inducing intramolecular skeletal rearrangement.
  • Electron paramagnetic resonance (EPR) spectroscopy.
  • Single-crystal X-ray diffraction.
  • UV/Vis spectroscopy.
  • Density functional theory (DFT) calculations.

Main Results:

  • Isolation of a crystalline dicarbondiphosphide-based β-distonic radical cation salt (3.+ (BARF)) stable at room temperature.
  • Experimental and computational validation of the structure and electronic properties.
  • Demonstration of significant spin density (0.74 a.u.) at a two-coordinate phosphorus atom and cationic charge (1.53 a.u.) at a four-coordinate phosphorus atom, separated by a carbon atom.

Conclusions:

  • The synthesized compound represents the closest isolable entity to a genuine phosphorus distonic radical cation reported to date.
  • This work provides a new platform for studying the fundamental properties of radical cations with separated charge and spin centers.