Oxatriquinacene

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Ball-and-stick model of the oxatriquinacene cation.
Space-filling model of the oxatriquinacene cation.

Oxatriquinacene is an organic cation with formula C
12
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.

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[edit]

References[edit]

  1. ^ a b Mark Mascal, Nema Hafezi, Nabin K. Meher, and James C. Fettinger (2008). "Oxatriquinane and Oxatriquinacene: Extraordinary Oxonium Ions". Journal of the American Chemical Society 130 (41): 13532–13533. doi:10.1021/ja805686u. PMID 18798616. 
  2. ^ Rachel Petkewich (September 29, 2008). "Taming Alkyl Oxonium Ions: Fused tricyclic structure stabilizes famously reactive alkylating agents". Chemical and Engineering News 86 (39): 10. doi:10.1021/cen-v086n039.p010. 
  3. ^ Tim Reid (3 October 2008). "Oxonium ions: Ring of stability". Nature Chemistry. doi:10.1038/nchem.70.