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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...
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...
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.
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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 Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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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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Trisphenalenyl-based neutral radical molecular conductor.

Sushanta K Pal1, Mikhail E Itkis, Fook S Tham

  • 1Department of Chemistry, University of California, Riverside, California 92521-0403, USA.

Journal of the American Chemical Society
|March 1, 2008
PubMed
Summary

Researchers synthesized and characterized novel tris(1,9-disubstituted phenalenyl)silicon neutral radicals. These molecules exhibit weak pi-dimer packing in the solid state and show antiferromagnetic coupling at low temperatures.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Solid-State Physics

Background:

  • Phenalenyl radicals are known for their unique electronic and magnetic properties.
  • The development of novel radical systems is crucial for advancing molecular electronics and spintronics.

Purpose of the Study:

  • To report the synthesis and characterization of a new family of tris(1,9-disubstituted phenalenyl)silicon neutral radicals.
  • To investigate the solid-state packing, magnetic properties, and electrical conductivity of these novel radicals.

Main Methods:

  • Single-crystal X-ray diffraction for structural analysis.
  • Magnetic susceptibility measurements to determine magnetic behavior.
  • Electrical conductivity measurements using a four-probe method.

Main Results:

  • The first member of the tris(1,9-disubstituted phenalenyl)silicon neutral radical family was successfully prepared and crystallized.
  • Solid-state characterization revealed weak partial pi-dimer packing with intermolecular C-C contacts near van der Waals distances.
  • Magnetic susceptibility indicated approximately 0.7 Curie spins per molecule, with antiferromagnetic coupling observed below 50 K.
  • Room-temperature single-crystal conductivity was measured at 2.4 x 10(-6) S cm(-1).

Conclusions:

  • The study presents a new class of silicon-centered neutral radicals with interesting solid-state properties.
  • The observed pi-dimerization and magnetic coupling suggest potential for applications in molecular materials.
  • Further research into structure-property relationships in this radical family is warranted.