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User:OrganoMetallurgy/Drafts/Phenalenyl radical

From Wikipedia, the free encyclopedia
Phenalenyl
Names
Other names
perinaphthyl, perinaphthenyl,
Identifiers
3D model (JSmol)
Abbreviations PLY
  • C1=CC2=C3C(=C1)C=C[CH]C3=CC=C2
Properties
C13H9
Molar mass 165.215 g·mol−1
Appearance yellow or blue solutions
UV-vismax) 613 nm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

non-chembox sections

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Phenalenyl is a stable aromatic hydrocarbon radical. It's of interest

It's stable in solution at room temperature in the absence of oxygen. It forms a σ-dimer in the solid state and at low temperatures in solution.

Properties

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Phenalenyl is a stable radical. Its stability is due to its aromaticity and the delocalization of the unpaired electron.

Structure

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Synthesis/Preparation

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The phenalenyl radical was first prepared in 1957 by the oxidation of phenalene dissolved in carbon tetrachloride by air. doi:10.1063/1.1743526 Another means of preparing it is the oxidation of the phenalenyl anion, prepared by the deprotonation of phenalene by potassium methoxide, by a limited amount of oxygen/air.

Applications/Uses

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Phenalenyl itself doesn't have any

Reactions

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The dimer can decompose to peropyrene Further oxidized to phenalone

History

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References

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[1]

  1. ^ Uchida, Kazuyuki; Kubo, Takashi (2016). "Recent Advances in the Chemistry of Phenalenyl". Journal of Synthetic Organic Chemistry, Japan. 74 (11): 1069–1077. doi:10.5059/yukigoseikyokaishi.74.1069.