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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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 molecule. These three...
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

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...
Radical Formation: Overview01:03

Radical Formation: Overview

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 latter, also known...
Radical Formation: Addition00:47

Radical Formation: Addition

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 unpaired...
Radical Formation: Abstraction00:47

Radical Formation: Abstraction

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...
VSEPR Theory and the Effect of Lone Pairs04:01

VSEPR Theory and the Effect of Lone Pairs

Effect of Lone Pairs of Electrons on Molecule Geometry

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Updated: May 13, 2026

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

Radical frustrated Lewis pairs.

Timothy H Warren1, Gerhard Erker

  • 1Department of Chemistry, Georgetown University, Washington, DC, USA, thw@georgetown.edu.

Topics in Current Chemistry
|March 8, 2013
PubMed
Summary

Researchers created novel radical adducts by capturing nitric oxide (NO) with frustrated Lewis pairs (FLPs). These FLP-NO species exhibit unique reactivity, enabling new applications in C-H functionalization and polymerization.

Area of Science:

  • Organometallic Chemistry
  • Radical Chemistry
  • Supramolecular Chemistry

Background:

  • Frustrated Lewis pairs (FLPs) typically react with diamagnetic unsaturated molecules.
  • Existing literature focuses on FLP adducts with alkenes, alkynes, and heterocumulenes.
  • Radical FLP chemistry remains less explored.

Purpose of the Study:

  • To investigate the capture of diatomic radical nitric oxide (NO) by intramolecular phosphane/borane FLPs.
  • To characterize the resulting radical FLP adducts and their reactivity.
  • To explore potential applications in catalysis and polymerization.

Main Methods:

  • Synthesis of intramolecular phosphane/borane FLPs.
  • Reaction of FLPs with nitric oxide (NO).

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Last Updated: May 13, 2026

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  • Characterization of FLP-NO adducts using spectroscopic techniques.
  • Evaluation of FLP-NO species in C-H functionalization and nitroxide-mediated polymerization.

    • Main Results:

    • Successful capture of NO by intramolecular FLPs, forming a new family of radical adducts.
    • Formation of heterocycles with novel P-N and B-N bonds.
    • Demonstration of spin density Umpolung of NO in FLP-NO species.
    • Observation of significant O-centered radical reactivity in FLP-NO adducts.
    • Successful application of FLP-NO species in H-atom abstraction/radical recombination C-H functionalization.
    • Deployment in nitroxide-mediated polymerization of alkenes.

    Conclusions:

    • Intramolecular FLPs can capture radical NO, expanding the scope of FLP chemistry.
    • FLP-NO adducts exhibit unique radical reactivity and enable new synthetic transformations.
    • Radical FLPs offer a versatile platform for catalysis and polymer synthesis.