Longest C–C Single Bond among Neutral Hydrocarbons with a Bond Length beyond 1.8 Å

Ishigaki, Yusuke; Shimajiri, Takuya; Takeda, Takashi; Katoono, Ryo; Suzuki, Takanori

Longest C–C Single Bond among Neutral Hydrocarbons with a Bond Length beyond 1.8 Å

Ishigaki, Yusuke; Shimajiri, Takuya; Takeda, Takashi et al.

Chem, 2018, 4(4), 795-806

Permalink : https://hdl.handle.net/2115/73547

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論文情報

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アクセス権	open access
URI	https://hdl.handle.net/2115/73547
タイトル	Longest C–C Single Bond among Neutral Hydrocarbons with a Bond Length beyond 1.8 Å
その他のタイトル	Longest C-C Single Bond among Neutral Hydrocarbons with a Bond Length beyond 1.8 angstrom
著者	Ishigaki, Yusuke ; Shimajiri, Takuya ; Takeda, Takashi ; Katoono, Ryo ; Suzuki, Takanori
e-Rad_Researcher 60776475 著者名 Ishigaki, Yusuke
著者名 Shimajiri, Takuya
著者名 Takeda, Takashi
e-Rad_Researcher 60432142 著者名 Katoono, Ryo
e-Rad_Researcher 70202132 著者名 Suzuki, Takanori
言語	英語
キーワード	long bond
	strained hydrocarbon
	extreme structure
	hexaphenylethane
	polycyclic hydrocarbons
	core-shell
	scissor effect
	DFT calculation
	X-ray analysis
	Raman spectroscopy
発行日	2018-04-12
収録物名	Chem
巻(号)	4(4)
ページ	795-806
抄録	On the basis of the intramolecular “core-shell strategy,” we designed dihydropyracylene with two spiro(dibenzocycloheptatriene) units, for which theoretical calculations predicted a very weak C–C bond with a bond length around 1.8 Å. This bond is expanded by the forced adoption of an eclipsed conformation and by angle strain through a “scissor effect.” The highly strained hydrocarbon was isolated as a thermally stable compound with no signs of diradical contribution because the weak C–C bond (core) is protected by the shape-persistent fused-ring structure (shell). A Raman shift corresponding to the C–C stretching vibration (587 cm−1) was very different from that for ethane (993 cm−1). The bond length determined by X-ray (1.806(2) Å) was greater than the shortest non-bonded intramolecular C…C contact (1.80(2) Å). The assumed limit for a C–C bond (1.803 Å) by supposing linear correlation between bond length and bond-dissociation energy for covalent bonding was proven to be invalid.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
権利情報	Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
権利情報	©2018. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
PISSN	2451-9294
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1016/j.chempr.2018.01.011