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Related Concept Videos

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...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Electron Paramagnetic Resonance (EPR) Spectroscopy: Organic Radicals01:17

Electron Paramagnetic Resonance (EPR) Spectroscopy: Organic Radicals

Ideally, an unpaired electron shows a single peak in the EPR spectrum due to the transition between the two spin energy states. However, coupling interactions can occur between the spins of the unpaired electron and any neighboring spin-active nuclei. This hyperfine coupling results in hyperfine splitting, where the EPR signal is split into multiplets. The signals split into 2nI + 1 peaks, where n is the number of equivalent nuclei and I is the nuclear spin. These splitting patterns provide...
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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 low‐energy SOMO, which interacts...
Noble Gases02:54

Noble Gases


The elements in group 18 are noble gases (helium, neon, argon, krypton, xenon, and radon). They earned the name “noble” because they were assumed to be nonreactive since they have filled valence shells. In 1962, Dr. Neil Bartlett at the University of British Columbia proved this assumption to be false.
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

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 factors, steric factors also account...

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Related Experiment Video

Updated: Jun 1, 2026

Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups
08:15

Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups

Published on: February 11, 2012

A neutral, monomeric germanium(I) radical.

William D Woodul1, Emma Carter, Robert Müller

  • 1School of Chemistry, Monash University, P.O. Box 23, Clayton, Melbourne, VIC 3800, Australia.

Journal of the American Chemical Society
|June 14, 2011
PubMed
Summary

Researchers synthesized the first monomeric, neutral germanium(I) radical complex, [((But)Nacnac)Ge:](•), using bulky β-diketiminato ligands. This discovery advances understanding of germanium radical chemistry.

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Theoretical Calculation and Experimental Verification for Dislocation Reduction in Germanium Epitaxial Layers with Semicylindrical Voids on Silicon
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

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Last Updated: Jun 1, 2026

Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups
08:15

Synthesis of Nine-atom Deltahedral Zintl Ions of Germanium and their Functionalization with Organic Groups

Published on: February 11, 2012

Theoretical Calculation and Experimental Verification for Dislocation Reduction in Germanium Epitaxial Layers with Semicylindrical Voids on Silicon
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Theoretical Calculation and Experimental Verification for Dislocation Reduction in Germanium Epitaxial Layers with Semicylindrical Voids on Silicon

Published on: July 17, 2020

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

Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Radical Chemistry

Background:

  • Germanium(II) complexes with bulky ligands are precursors to novel germanium species.
  • The synthesis and characterization of low-valent germanium radicals remain challenging.
  • β-diketiminato ligands offer steric protection and electronic tunability for metal centers.

Purpose of the Study:

  • To synthesize and characterize a monomeric, neutral germanium(I) radical complex.
  • To investigate the electronic structure and properties of the germanium(I) radical.
  • To explore the reactivity of the novel germanium radical species.

Main Methods:

  • Stoichiometric reduction of a germanium(II) chloride complex using sodium naphthalenide or a magnesium(I) dimer.
  • X-ray crystallography for structural determination.
  • Electron Paramagnetic Resonance (EPR) and Electron Nuclear Double Resonance (ENDOR) spectroscopy for electronic characterization.
  • Computational studies (e.g., DFT) to understand bonding and electronic structure.
  • Reactivity studies to probe the chemical behavior of the germanium radical.

Main Results:

  • Successful synthesis of the radical complex [((But)Nacnac)Ge:](•) in moderate yields.
  • Structural confirmation of a monomeric, neutral germanium(I) species.
  • Spectroscopic and computational data provide evidence for a germanium(I) radical character.
  • Demonstration of the stability and unique electronic properties of the germanium radical.

Conclusions:

  • The study reports the first authenticated monomeric, neutral germanium(I) radical.
  • The findings expand the known chemistry of low-valent main group radicals.
  • This germanium(I) radical serves as a platform for future investigations into germanium radical chemistry and applications.