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Cyclo(18)carbon






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This is an old revision of this page, as edited by ZxxZxxZ (talk | contribs)at15:52, 17 August 2019 (top). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.
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Cyclo(18)carbon
Identifiers

3D model (JSmol)

PubChem CID

CompTox Dashboard (EPA)

  • 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

  • Alternating form: 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-nonayneorcyclo[18]carbon is a chemical compound, an allotrope of carbon with molecular formula C
18
. The molecule is a ring of eightteen 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][2]

An collaboration of teams at IBM and Oxford University team claimed to synthesize it in solid state in 2019[3]byelectrochemical decarbonylation of several sites of a cyclobutanone structure:[4]

Synthesis of cyclocarbon
Synthesis of cyclocarbon

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

  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.
  • ^ 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.
  • ^ Kaiser, Katharina (15 Aug 2019). "An sp-hybridized molecular carbon allotrope, cyclo[18]carbon". Science. doi:10.1126/science.aay1914.
  • ^ a b Castelvecchi, Davide (15 August 2019). "Chemists make first-ever ring of pure carbon". Nature. doi:10.1038/d41586-019-02473-z. Retrieved 16 August 2019.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Cyclo(18)carbon&oldid=911248275"

    Categories: 
    Aromatic compounds
    Group IV semiconductors
    Polyynes
    Cyclocarbons
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    This page was last edited on 17 August 2019, at 15:52 (UTC).

    This version of the page has been revised. Besides normal editing, the reason for revision may have been that this version contains factual inaccuracies, vandalism, or material not compatible with the Creative Commons Attribution-ShareAlike License.



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