User:OrganoMetallurgy/Drafts/Phenalenyl radical

Phenalenyl

Names
Other names perinaphthyl, perinaphthenyl,
Identifiers
3D model (JSmol)	Interactive image
Abbreviations	PLY
PubChem CID	13027868
SMILES C1=CC2=C3C(=C1)C=C[CH]C3=CC=C2
Properties
Chemical formula	C13H9
Molar mass	165.215 g·mol−1
Appearance	yellow or blue solutions
UV-vis (λmax)	613 nm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

non-chembox sections

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

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

Synthesis/Preparation

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

Phenalenyl itself doesn't have any

Reactions

The dimer can decompose to peropyrene Further oxidized to phenalone