Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.9K
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...
2.9K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.5K
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...
2.5K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.7K
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...
2.7K
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: Addition00:47

Radical Formation: Addition

2.3K
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...
2.3K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

6.7K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
6.7K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Crystal structure of the <i>meso</i> compound (2<i>R</i>,6<i>S</i>)-4-(5-bromo-pyrimidin-2-yl)-2,6-di-methyl-morpholine.

Acta crystallographica. Section E, Crystallographic communications·2026
Same author

4-[4-(4-Chloro-1,2,5-thia-diazol-3-yl)phen-yl]morpholine.

IUCrData·2026
Same author

Cytochrome P450-Mediated Metabolism of Antimycobacterial <i>N</i>α-Aroyl-<i>N</i>-aryl-phenylalanine Amides.

ACS infectious diseases·2026
Same author

Enantioselective synthesis of configurationally stable [5]helicenes containing 1,2-azaborine units.

Chemical science·2026
Same author

Amelioration of acute liver failure by a cinnamic acid derivative through inhibition of the ROS-NETosis axis.

Molecular biomedicine·2026
Same author

Nucleophilic substitution of a phthalimidyl group with morpholine in an N<sup>1</sup>-methyl-1,2,3-triazole: crystallographic evidence for migration of the methylene bridge.

Acta crystallographica. Section C, Structural chemistry·2026

Related Experiment Video

Updated: Mar 1, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.8K

α-Radical Phosphines: Synthesis, Structure, and Reactivity.

Lianghu Gu1, Yiying Zheng2, Estela Haldón2

  • 1Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstr 2, 37077, Göttingen, Germany.

Angewandte Chemie (International Ed. in English)
|May 26, 2017
PubMed
Summary

Researchers synthesized novel phosphines with persistent radicals using stable cyclic (alkyl)(amino)carbenes (cAACs). These α-radical phosphines show potential as spin-labeled ligands, demonstrated with gold(I) complexes.

Keywords:
X-ray crystallographycarbenesgold complexesradicalsα-radical phosphines

More Related Videos

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

8.3K
Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
14:07

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

14.2K

Related Experiment Videos

Last Updated: Mar 1, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.8K
Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

8.3K
Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
14:07

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

14.2K

Area of Science:

  • Organophosphorus Chemistry
  • Carbene Chemistry
  • Radical Chemistry
  • Coordination Chemistry

Background:

  • Persistent radicals are crucial in various chemical applications, including catalysis and materials science.
  • Stable cyclic (alkyl)(amino)carbenes (cAACs) are versatile building blocks in modern synthetic chemistry.
  • The development of novel ligands with unique electronic and magnetic properties is an ongoing area of research.

Purpose of the Study:

  • To synthesize and characterize a new class of phosphines incorporating persistent radicals.
  • To investigate the electronic and structural properties of these α-radical phosphines.
  • To explore the utility of these phosphines as spin-labeled ligands in coordination chemistry.

Main Methods:

  • Two-step synthesis involving condensation of chlorophosphines with cAACs, followed by reduction.
  • Structural, spectroscopic (NMR, EPR), and computational analyses (DFT) to characterize the compounds.
  • Preparation and single-crystal X-ray diffraction of gold(I) complexes featuring the α-radical phosphine ligands.

Main Results:

  • Successful synthesis of phosphines with persistent radicals, where spin density is localized on the α-carbon.
  • Characterization confirmed the α-position of the radical relative to the phosphorus atom.
  • Gold(I) complexes were prepared, demonstrating the ligands' coordination ability and potential for spin labeling.

Conclusions:

  • A novel series of α-radical phosphines has been developed, offering a new platform for radical chemistry.
  • These phosphines exhibit unique electronic structures with spin density primarily on the carbene carbon.
  • The demonstrated utility in forming gold(I) complexes highlights their potential as spin-labeled ligands for advanced applications.