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Related Concept Videos

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.
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...
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Radical Reactivity: Steric Effects01:10

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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.
Along with electronic...
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Radical Halogenation: Stereochemistry01:33

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Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
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Radical Reactivity: Overview01:11

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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...
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Radial System Protection01:23

Radial System Protection

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Radial systems employ time-delay overcurrent relays to reduce load interruptions. When a fault occurs, the nearest breaker opens first, while upstream breakers remain closed due to longer delay settings. This approach ensures minimal disruption to the rest of the system.
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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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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...
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Related Experiment Video

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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[5]Radialene.

Emily G Mackay1, Christopher G Newton1, Henry Toombs-Ruane1

  • 1Research School of Chemistry, Australian National University , Canberra, Australian Capital Territory 2601, Australia.

Journal of the American Chemical Society
|September 15, 2015
PubMed
Summary
This summary is machine-generated.

Researchers synthesized the elusive [5]radialene hydrocarbon for the first time. This breakthrough in carbocyclic chemistry overcomes previous synthetic failures, opening new avenues for studying these unique compounds.

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Area of Science:

  • Organic Chemistry
  • Carbocyclic Chemistry
  • Synthetic Chemistry

Background:

  • Radialenes are [n]-membered carbocyclic structures characterized by radiating alkenes.
  • While [3]-, [4]-, and [6]radialenes are known, synthesis of the five-membered [5]radialene has been unsuccessful.
  • These compounds have garnered significant synthetic and theoretical interest.

Purpose of the Study:

  • To achieve the first successful synthesis of the fundamental hydrocarbon [5]radialene (C10H10).
  • To explore novel synthetic strategies deviating from traditional high-temperature methods.
  • To investigate the inherent reactivity and stability of [5]radialene.

Main Methods:

  • Development of a novel synthetic route involving low-temperature decomplexation of a stable organometallic precursor.
  • Guidance from analysis of prior radialene synthesis challenges, including oxygen sensitivity.
  • Utilizing ab initio calculations to predict and understand the reactivity of [5]radialene.

Main Results:

  • Successful synthesis of the fundamental hydrocarbon [5]radialene (C10H10).
  • The synthetic approach utilized low-temperature organometallic decomplexation, a novel method for radialenes.
  • Calculations revealed [5]radialene's high susceptibility to Diels-Alder dimerization/polymerization due to low distortion energy and a narrow HOMO-LUMO gap.

Conclusions:

  • The first synthesis of [5]radialene was accomplished, filling a significant gap in radialene chemistry.
  • The unique reactivity of [5]radialene, particularly its propensity for Diels-Alder reactions, is attributed to its electronic and structural properties.
  • This work provides a foundation for further investigation into the properties and applications of [5]radialenes.