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OrganoMetallurgy/Drafts/2,5,8-Tri-tert-butyl-phenalenyl
Identifiers
Properties
Chemical formula	C25H33
Molar mass	333.539 g·mol−1
Appearance	deep blue crystals
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2,5,8-Tri-tert-butyl-phenalenyl is a stable phenalenyl radical. It is stable against the formation of σ bonded dimers due to the steric bulk of its tert-butyl groups, but forms face to face π dimers in solid state. Crystals slowly decompose in air. It was the first phenalenyl radical crystallized. ^[1]^[2]

Properties

Structure

Synthesis/Preparation

Applications

Reactions

History

References

^ Goto, Kosaburo; Kubo, Takashi; Yamamoto, Kagetoshi; Nakasuji, Kazuhiro; Sato, Kazunobu; Shiomi, Daisuke; Takui, Takeji; Kubota, Mari; Kobayashi, Tunetoshi (1999-02-01). "A Stable Neutral Hydrocarbon Radical: Synthesis, Crystal Structure, and Physical Properties of 2,5,8-Tri-tert-butyl-phenalenyl". Journal of the American Chemical Society. 121 (7): 1619–1620. doi:10.1021/ja9836242. ISSN 0002-7863.
^ Suzuki, Shuichi; Morita, Yasushi; Fukui, Kozo; Sato, Kazunobu; Shiomi, Daisuke; Takui, Takeji; Nakasuji, Kazuhiro (2006-03-01). "Aromaticity on the Pancake-Bonded Dimer of Neutral Phenalenyl Radical as Studied by MS and NMR Spectroscopies and NICS Analysis". Journal of the American Chemical Society. 128 (8): 2530–2531. doi:10.1021/ja058387z. ISSN 0002-7863.

[1] Goto, Kosaburo; Kubo, Takashi; Yamamoto, Kagetoshi; Nakasuji, Kazuhiro; Sato, Kazunobu; Shiomi, Daisuke; Takui, Takeji; Kubota, Mari; Kobayashi, Tunetoshi (1999-02-01). "A Stable Neutral Hydrocarbon Radical: Synthesis, Crystal Structure, and Physical Properties of 2,5,8-Tri-tert-butyl-phenalenyl". Journal of the American Chemical Society. 121 (7): 1619–1620. doi:10.1021/ja9836242. ISSN 0002-7863.

[2] Suzuki, Shuichi; Morita, Yasushi; Fukui, Kozo; Sato, Kazunobu; Shiomi, Daisuke; Takui, Takeji; Nakasuji, Kazuhiro (2006-03-01). "Aromaticity on the Pancake-Bonded Dimer of Neutral Phenalenyl Radical as Studied by MS and NMR Spectroscopies and NICS Analysis". Journal of the American Chemical Society. 128 (8): 2530–2531. doi:10.1021/ja058387z. ISSN 0002-7863.

[1]

[2]