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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...
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...
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: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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 instance, consider...
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak carbon–halogen...

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Related Experiment Video

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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

Bisdithiazolyl radical spin ladders.

Kristina Lekin1, Joanne W L Wong, Stephen M Winter

  • 1Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada.

Inorganic Chemistry
|February 9, 2013
PubMed
Summary
This summary is machine-generated.

Four new bisdithiazolyl radicals were synthesized and structurally characterized. Longer alkyl chains promote the formation of spin ladder arrays with strong antiferromagnetic coupling, consistent with theoretical models.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Solid-State Physics

Background:

  • Bisdithiazolyl radicals are organic molecules with interesting magnetic properties.
  • Controlling molecular packing in the solid state is crucial for tuning magnetic behavior.
  • Understanding intermolecular interactions is key to designing novel magnetic materials.

Purpose of the Study:

  • To synthesize and characterize a series of bisdithiazolyl radicals with varying alkyl chain lengths.
  • To investigate the impact of molecular structure on crystal packing and magnetic properties.
  • To elucidate the magnetic coupling mechanisms in these radical systems.

Main Methods:

  • X-ray crystallography for detailed structural analysis of the synthesized radicals.
  • Variable temperature magnetic susceptibility measurements to probe magnetic behavior.
  • Broken-symmetry Density Functional Theory (DFT) calculations to determine exchange interactions.

Main Results:

  • Crystal structures revealed slipped π-stack arrangements and intermolecular F···S bridges.
  • Compounds with longer alkyl chains (1b-d) formed spin ladder arrays.
  • Magnetic susceptibility data indicated antiferromagnetic coupling, fitting the Johnston spin ladder model for 1b-d.

Conclusions:

  • Alkyl chain length significantly influences crystal packing and the formation of spin ladder structures.
  • Strong antiferromagnetic interactions within the spin ladders dominate the magnetic properties.
  • DFT calculations confirm the observed magnetic coupling and provide insights into the electronic structure.