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

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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
polycyclic hydrocarbons
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
Type: article (author version)
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

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