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Related Concept Videos

Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.8K
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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Radical Formation: Addition00:47

Radical Formation: Addition

2.1K
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...
2.1K
Radical Formation: Overview01:03

Radical Formation: Overview

2.5K
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...
2.5K
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...
2.5K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.3K
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...
2.3K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.3K
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...
2.3K

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Related Experiment Video

Updated: Dec 15, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

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A diradical based on odd-electron σ-bonds.

Wenbang Yang1, Li Zhang1,2, Dengmengfei Xiao3

  • 1State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Advanced Microstructures, Nanjing University, Nanjing, 210023, China.

Nature Communications
|July 12, 2020
PubMed
Summary
This summary is machine-generated.

Researchers report the first diradical stabilized by odd-electron selenium-selenium bonds. This discovery challenges previous understanding of diradical structures and opens new avenues in radical chemistry.

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Last Updated: Dec 15, 2025

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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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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Area of Science:

  • Inorganic Chemistry
  • Theoretical Chemistry
  • Materials Science

Background:

  • Odd-electron bonds, including one-electron and three-electron sigma bonds, are crucial intermediates in various chemical processes.
  • Stable diradicals, characterized by unpaired electrons, are typically based on localized s/p orbitals or delocalized pi systems.
  • The isolation of diradicals specifically based on odd-electron sigma bonds has remained an elusive goal in chemistry.

Purpose of the Study:

  • To report the synthesis and characterization of a novel dication diradical stabilized by three-electron selenium-selenium sigma bonds.
  • To investigate the electronic structure and bonding in this unique diradical species.
  • To compare the behavior of the selenium-based diradical with its sulfur analogue.

Main Methods:

  • Computational chemistry calculations to model the electronic structure and bonding.
  • Spectroscopic techniques for characterization.
  • Synthesis of selenium and sulfur dication compounds.

Main Results:

  • A stable dication diradical featuring two Se∴Se three-electron sigma bonds was successfully synthesized and characterized.
  • The electronic structure confirms the diradical nature arising from these unique odd-electron bonds.
  • The analogous sulfur dication exhibited closed-shell singlet behavior, lacking diradical character.

Conclusions:

  • This work presents the first definitive example of a diradical stabilized by odd-electron sigma bonds, specifically using selenium.
  • The findings expand the known structural motifs for stable diradicals.
  • The contrasting behavior between the selenium and sulfur analogues highlights the unique role of heavier chalcogens in stabilizing unusual bonding arrangements.