Cyclo(18)carbon

Cyclo[18]carbon
Names
	Preferred IUPAC name Cyclooctadeca-1,3,5,7,9,11,13,15,17-nonayne
Identifiers
CAS Number	126487-09-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	74015635;
PubChem CID	14940714;
CompTox Dashboard (EPA)	DTXSID801267863 ;
	InChI InChI=1S/C18/c1-2-4-6-8-10-12-14-16-18-17-15-13-11-9-7-5-3-1 Key: GPWDPLKISXZVIE-UHFFFAOYSA-N;
	SMILES C1#CC#CC#CC#CC#CC#CC#CC#CC#C1;
Properties
Chemical formula	C18
Molar mass	216.198 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cyclooctadeca-1,3,5,7,9,11,13,15,17-nonayne or cyclo[18]carbon is an allotrope of carbon with molecular formula C
₁₈. The molecule is a ring of eighteen carbon atoms, connected by alternating triple and single bonds; thus, it is a polyyne and a cyclocarbon.

Cyclo[18]carbon is the smallest cyclo[n]carbon predicted to be thermodynamically stable, with a computed strain energy of 72 kilocalories per mole.^[1] Above 122 K, it explosively decomposes to amorphous graphite.^[2]

A collaboration of teams at IBM and the University of Oxford team claimed to synthesize it in solid state in 2019^[3] by electrochemical decarbonylation of several sites of a cyclobutanone structure:^[4] Later, researchers from Spain have used computational techniques to probe the structural and electronic properties of the molecule, and have discovered it to be an electron acceptor.^[5]

According to these IBM researchers, the electronic structure of their product consists of alternating triple bonds and single bonds, rather than a cumulene-type structure of consecutive double bonds. This supposedly makes this molecule a semiconductor.^[4]

References

^ George A. Adamson; Charles W. Rees (1996). "Towards the total synthesis of cyclo[n]carbons and the generation of cyclo[6]carbon". J. Chem. Soc., Perkin Trans. 1 (13): 1535–1543. doi:10.1039/P19960001535.
^ François Diederich; Yves Rubin; Carolyn B. Knobler; Robert L. Whetten; Kenneth E. Schriver; Kendall N. Houk; Yi Li (8 September 1989). "All-Carbon Molecules: Evidence for the Generation of Cyclo[18]carbon from a Stable Organic Precursor". Science. 245 (4922): 1088–1090. Bibcode:1989Sci...245.1088D. doi:10.1126/science.245.4922.1088. PMID 17838807. S2CID 23726682.
^ Kaiser, Katharina; Scriven, Lorel M.; Schulz, Fabian; Gawel, Przemyslaw; Gross, Leo; Anderson, Harry L. (15 Aug 2019). "An sp-hybridized molecular carbon allotrope, cyclo[18]carbon". Science. 365 (6459): 1299–1301. arXiv:1908.05904. doi:10.1126/science.aay1914. PMID 31416933. S2CID 201019470.
^ ^a ^b Castelvecchi, Davide (15 August 2019). "Chemists make first-ever ring of pure carbon". Nature. 572 (7770): 426. doi:10.1038/d41586-019-02473-z. PMID 31431741.
^ Stasyuk, Anton J.; Stasyuk, Olga A.; Solà, Miquel; Voityuk, Alexander A. (29 Nov 2019). "Cyclo[18]carbon: the smallest all-carbon electron acceptor". Chemical Communications. 56 (3): 352–355. doi:10.1039/c9cc08399e. hdl:10256/17613. PMID 31825030. S2CID 209316603.

[adaree-1] George A. Adamson; Charles W. Rees (1996). "Towards the total synthesis of cyclo[n]carbons and the generation of cyclo[6]carbon". J. Chem. Soc., Perkin Trans. 1 (13): 1535–1543. doi:10.1039/P19960001535.

[diederich89-2] François Diederich; Yves Rubin; Carolyn B. Knobler; Robert L. Whetten; Kenneth E. Schriver; Kendall N. Houk; Yi Li (8 September 1989). "All-Carbon Molecules: Evidence for the Generation of Cyclo[18]carbon from a Stable Organic Precursor". Science. 245 (4922): 1088–1090. Bibcode:1989Sci...245.1088D. doi:10.1126/science.245.4922.1088. PMID 17838807. S2CID 23726682.

[3] Kaiser, Katharina; Scriven, Lorel M.; Schulz, Fabian; Gawel, Przemyslaw; Gross, Leo; Anderson, Harry L. (15 Aug 2019). "An sp-hybridized molecular carbon allotrope, cyclo[18]carbon". Science. 365 (6459): 1299–1301. arXiv:1908.05904. doi:10.1126/science.aay1914. PMID 31416933. S2CID 201019470.

[Castelvecchi-4] Castelvecchi, Davide (15 August 2019). "Chemists make first-ever ring of pure carbon". Nature. 572 (7770): 426. doi:10.1038/d41586-019-02473-z. PMID 31431741.

[5] Stasyuk, Anton J.; Stasyuk, Olga A.; Solà, Miquel; Voityuk, Alexander A. (29 Nov 2019). "Cyclo[18]carbon: the smallest all-carbon electron acceptor". Chemical Communications. 56 (3): 352–355. doi:10.1039/c9cc08399e. hdl:10256/17613. PMID 31825030. S2CID 209316603.

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