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

doi:10.1016/j.chempr.2018.01.011


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

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Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/73547

Title:	Longest C–C Single Bond among Neutral Hydrocarbons with a Bond Length beyond 1.8 Å
Authors:	Ishigaki, Yusuke Browse this author →KAKEN DB
	Shimajiri, Takuya Browse this author
	Takeda, Takashi Browse this author
	Katoono, Ryo Browse this author →KAKEN DB
	Suzuki, Takanori Browse this author →KAKEN DB
Keywords:	long bond
	strained hydrocarbon
	extreme structure
	hexaphenylethane
	polycyclic hydrocarbons
	core-shell
	scissor effect
	DFT calculation
	X-ray analysis
	Raman spectroscopy
Issue Date:	12-Apr-2018
Journal Title:	Chem
Volume:	4
Issue:	4
Start Page:	795
End Page:	806
Publisher DOI:	10.1016/j.chempr.2018.01.011
Abstract:	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.
Rights:	©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/
Rights:	https://creativecommons.org/licenses/by-nc-nd/4.0/
Type:	article (author version)
URI:	http://hdl.handle.net/2115/73547
Appears in Collections:	理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 石垣侑祐・鈴木孝紀

OAI-PMH ( junii2 , jpcoar_1.0 )

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