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词条 Oxatriquinacene
释义

  1. See also

  2. References

{{Chembox
| ImageFile = Oxatriquinacene.svg
| ImageSize = 140
| ImageAlt = Skeletal formula of the oxatriquinacene cation
| ImageFile1 = Oxatriquinacene cation 3D ball.png
| ImageSize1 = 160
| ImageAlt1 = Ball-and-stick model of the oxatriquinacene cation
| IUPACName = (2as,4as,6as)-4a,6a-Dihydro-2aH-6b-oxoniacyclopenta[cd]pentalene
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo =
| PubChem =
| ChemSpiderID = 32675183
| SMILES = C1=C[C@@H]2[O+]3[C@H]1C=C[C@@H]3C=C2
| InChI = 1/C9H9O/c1-2-8-5-6-9-4-3-7(1)10(8)9/h1-9H/q+1/t7-,8+,9-
| InChIKey = YQBOZXASCNTXGC-AYMMMOKOBA
| StdInChI = 1S/C9H9O/c1-2-8-5-6-9-4-3-7(1)10(8)9/h1-9H/q+1/t7-,8+,9-
| StdInChIKey = YQBOZXASCNTXGC-AYMMMOKOSA-N
|Section2={{Chembox Properties
| Formula = C9H9O
| MolarMass = 133.167
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

Oxatriquinacene is an organic cation with formula {{chem|C|9|H|9|O|+}}. It is an oxonium ion, with a trivalent oxygen atom with +1 charge connected to carbons 1,4, and 7 of a cyclononatriene ring, forming three fused pentagonal cycles. The compound may possess weak tris-homoaromatic character.

Oxatriquinacene has remarkable stability compared to other oxonium cations, although not as extreme as that of the similar oxatriquinane. It reacts with water, but can be dissolved in acetonitrile. It is of interest as a possible precursor to oxaacepentalene, a hypothetical neutral aromatic species.[1]

Oxatriquinacene was obtained in 2008 by Mascal and others, through a variant of the synthesis that led them to oxatriquinane.[1][2][3]

See also

  • Triethyloxonium tetrafluoroborate
  • Brookhart's acid
  • Pyrylium salt

References

1. ^ {{cite journal |title=Oxatriquinane and Oxatriquinacene: Extraordinary Oxonium Ions |author1=Mark Mascal |author2=Nema Hafezi |author3=Nabin K. Meher |author4=James C. Fettinger |last-author-amp=yes |pages=13532–13533 |doi=10.1021/ja805686u |volume=130 |year=2008 |journal=Journal of the American Chemical Society |pmid=18798616 |issue=41}}
2. ^ {{cite journal |date=September 29, 2008 |volume=86 |issue=39 |pages=10 |title=Taming Alkyl Oxonium Ions: Fused tricyclic structure stabilizes famously reactive alkylating agents |author=Rachel Petkewich |journal=Chemical and Engineering News |url=http://pubs.acs.org/cen/news/86/i39/8639notw6.html |doi=10.1021/cen-v086n039.p010}}
3. ^ {{cite journal |journal=Nature Chemistry |title=Oxonium ions: Ring of stability |author=Tim Reid |doi=10.1038/nchem.70 |date=3 October 2008}}

1 : Oxycations

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