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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.
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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.
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Radical Halogenation: Stereochemistry01:33

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Aromatic Hydrocarbon Cations: Structural Overview01:18

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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 Substitution: Allylic Chlorination01:31

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Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Diaryldichalcogenide radical cations.

Ole Mallow1, Monther A Khanfar2,3, Moritz Malischewski2

  • 1Institut für Anorganische Chemie , Universität Bremen , Leobener Straße , 28359 Bremen , Germany .

Chemical Science
|September 23, 2017
PubMed
Summary
This summary is machine-generated.

Researchers studied one-electron oxidation of diaryldichalcogenides, forming radical cations. Stable radical cations were synthesized from sterically hindered diaryldichalcogenides, offering insights into their properties.

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Area of Science:

  • Organometallic Chemistry
  • Materials Science
  • Spectroscopy

Background:

  • Diaryldichalcogenides are compounds containing two chalcogen atoms (sulfur, selenium, or tellurium) linked together and bonded to aryl groups.
  • Understanding the oxidation behavior of these compounds is crucial for developing new materials with specific electronic properties.

Purpose of the Study:

  • To investigate the one-electron oxidation of two series of diaryldichalcogenides: (C6F5E)2 and (2,6-Mes2C6H3E)2, where E = S, Se, Te.
  • To synthesize and characterize the resulting radical cations and study their electronic and structural properties.

Main Methods:

  • One-electron oxidation reactions using strong oxidizing agents like AsF5, SbF5, and [NO][SbF6].
  • Isolation and characterization of radical cations as salts (e.g., [Sb2F11]-, [As2F11]-, [SbF6]-).
  • X-ray diffraction analysis, Electron Paramagnetic Resonance (EPR) spectroscopy, and Density Functional Theory (DFT) calculations.

Main Results:

  • Thermally unstable radical cations were formed from (C6F5E)2 series with AsF5/SbF5, except for the tellurium compound which yielded a Te-C bond cleavage product.
  • Thermally stable radical cations were synthesized in high yields from (2,6-Mes2C6H3E)2 series using [NO][SbF6].
  • Detailed electronic and structural properties of the synthesized radical cations were elucidated through various analytical techniques.

Conclusions:

  • The steric hindrance around the dichalcogenide core significantly influences the stability of the resulting radical cations.
  • The study successfully generated and characterized novel radical cations, expanding the understanding of chalcogen-based radical chemistry.
  • The findings provide a foundation for designing and synthesizing new materials with tunable electronic and optical properties based on diaryldichalcogenide radical cations.