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Related Concept Videos

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.
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 Reactivity: Overview01:11

Radical Reactivity: Overview

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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 Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.2K
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...
2.2K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

4.0K
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.
4.0K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.9K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.9K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.4K
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...
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Updated: Nov 26, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Dynamic Nuclear Polarization Using 3D Aromatic Boron Cluster Radicals.

Yaewon Kim1,2, Rebecca Kubena3, Jonathan Axtell3

  • 1Department of Chemistry, Texas A&M University, 3255 TAMU, College Station, Texas 77843, United States.

The Journal of Physical Chemistry Letters
|December 9, 2020
PubMed
Summary
This summary is machine-generated.

New dodecaborate cluster radicals enhance nuclear magnetic resonance (NMR) signals for reactive compounds. This breakthrough in dissolution dynamic nuclear polarization (D-DNP) offers superior chemical compatibility for advanced reaction monitoring.

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Preparation of Fungal and Plant Materials for Structural Elucidation Using Dynamic Nuclear Polarization Solid-State NMR
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Area of Science:

  • Chemistry
  • Materials Science
  • Spectroscopy

Background:

  • Dynamic Nuclear Polarization (DNP) enhances Nuclear Magnetic Resonance (NMR) signals.
  • Conventional DNP relies on radical species like TEMPO, which have limited chemical compatibility.
  • Developing new radical systems compatible with reactive compounds is crucial for expanding DNP applications.

Purpose of the Study:

  • To investigate dodecaborate [B12(OR)12]1- radical cluster anions as novel agents for DNP.
  • To evaluate the ability of these clusters to enhance 19F NMR signals.
  • To demonstrate the chemical compatibility of these radicals with reactive compounds like Lewis acids.

Main Methods:

  • Synthesis of dodecaborate [B12(OR)12]1- radical cluster anions with fluorinated end-groups.
  • Application of dissolution dynamic nuclear polarization (D-DNP) technique.
  • Liquid-state NMR spectroscopy experiments at 9.4 Tesla to measure signal enhancement.

Main Results:

  • Dodeca-borate clusters successfully enhanced 19F NMR signals.
  • Achieved significant signal enhancement (1000-2000 times) for B(C6F5)3, a Lewis acid.
  • Demonstrated superior chemical compatibility compared to TEMPO with reactive species.

Conclusions:

  • 3D aromatic dodecaborate radicals are effective for DNP and hyperpolarizing reactive compounds.
  • These radicals offer advantages over conventional DNP agents due to enhanced chemical compatibility.
  • Opens new avenues for reaction monitoring using D-DNP NMR, including observing catalytic species.