Cyclo(6)carbon

Cyclo(6)carbon
Names
	Preferred IUPAC name Hexadehydrobenzene
Identifiers
CAS Number	21894-87-1;
3D model (JSmol)	Alternating form: Interactive image; Cumulene form: Interactive image;
ChemSpider	25934244;
PubChem CID	12334440;
CompTox Dashboard (EPA)	DTXSID70491042;
	InChI InChI=1S/C6/c1-2-4-6-5-3-1 Key: PXCDDPIOUAJVRE-UHFFFAOYSA-N ;
	SMILES Alternating form: C1#CC#CC#C1; Cumulene form: C1=C=C=C=C=C=1;
Properties
Chemical formula	C6
Molar mass	72.066 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Cyclo[6]carbon is an allotrope of carbon with molecular formula C₆. The molecule is a ring of six carbon atoms, connected by alternating double bonds.^[1] It is, therefore, a member of the cyclo[n]carbon family.

There have been a few attempts to synthesize cyclo[6]carbon, e.g. by pyrolysis of mellitic anhydride,^[2] but without success until 2023, when it was successfully synthesized by atom manipulation of hexachlorobenzene.^[1]

Calculations suggest that the alternative cyclic cumulene structure, called cyclohexahexaene, is the potential energy minimum of the cyclo[6]carbon framework.^[3]

References

^ ^a ^b Xu, Wei; Sun, Luye; Zheng, Wei; Gao, Wenze; Kang, Faming (2023-10-05), On-surface synthesis of anti-aromatic cyclo[12]carbon and aromatic cyclo[6]carbon (PDF), doi:10.21203/rs.3.rs-3411973/v1
^ Fields, Ellis K.; Meyerson, Seymour (October 1966). "Arynes by Pyrolysis of Acid Anhydrides". J. Org. Chem. 31 (10): 3307–3309. doi:10.1021/jo01348a046.3307-3309&rft.date=1966-10&rft_id=info:doi/10.1021/jo01348a046&rft.aulast=Fields&rft.aufirst=Ellis K.&rft.au=Meyerson, Seymour&rfr_id=info:sid/en.wikipedia.org:Cyclo(6)carbon" class="Z3988">
^ Zahradník, Rudolf; Hobza, Pavel; Burcl, Rudolf; Andes Hess, B. (October 1994). "Strained unsaturated molecules. Theoretical study of acyclic and cyclic cumulenes and acetylenes". Journal of Molecular Structure: THEOCHEM. 313 (3): 335–349. doi:10.1016/0166-1280(94)85015-1.335-349&rft.date=1994-10&rft_id=info:doi/10.1016/0166-1280(94)85015-1&rft.aulast=Zahradník&rft.aufirst=Rudolf&rft.au=Hobza, Pavel&rft.au=Burcl, Rudolf&rft.au=Andes Hess, B.&rfr_id=info:sid/en.wikipedia.org:Cyclo(6)carbon" class="Z3988">

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[Xu-1] Xu, Wei; Sun, Luye; Zheng, Wei; Gao, Wenze; Kang, Faming (2023-10-05), On-surface synthesis of anti-aromatic cyclo[12]carbon and aromatic cyclo[6]carbon (PDF), doi:10.21203/rs.3.rs-3411973/v1

[2] Fields, Ellis K.; Meyerson, Seymour (October 1966). "Arynes by Pyrolysis of Acid Anhydrides". J. Org. Chem. 31 (10): 3307–3309. doi:10.1021/jo01348a046.3307-3309&rft.date=1966-10&rft_id=info:doi/10.1021/jo01348a046&rft.aulast=Fields&rft.aufirst=Ellis K.&rft.au=Meyerson, Seymour&rfr_id=info:sid/en.wikipedia.org:Cyclo(6)carbon" class="Z3988">

[3] Zahradník, Rudolf; Hobza, Pavel; Burcl, Rudolf; Andes Hess, B. (October 1994). "Strained unsaturated molecules. Theoretical study of acyclic and cyclic cumulenes and acetylenes". Journal of Molecular Structure: THEOCHEM. 313 (3): 335–349. doi:10.1016/0166-1280(94)85015-1.335-349&rft.date=1994-10&rft_id=info:doi/10.1016/0166-1280(94)85015-1&rft.aulast=Zahradník&rft.aufirst=Rudolf&rft.au=Hobza, Pavel&rft.au=Burcl, Rudolf&rft.au=Andes Hess, B.&rfr_id=info:sid/en.wikipedia.org:Cyclo(6)carbon" class="Z3988">

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