Oxatriquinacene

Oxonium ion From Wikipedia, the free encyclopedia

Oxatriquinacene

Oxatriquinacene is an organic cation with formula C
9
H
9
O+
. It is an oxonium ion, with a tricoordinated 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.

Quick Facts Names, Identifiers ...
Oxatriquinacene
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Names
Preferred IUPAC name
(2as,4as,6as)-4a,6a-Dihydro-2a1λ4-oxacyclopenta[cd]pentalen-2a1(2aH)-ylium
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C9H9O/c1-2-8-5-6-9-4-3-7(1)10(8)9/h1-9H/q+1/t7-,8+,9-
    Key: YQBOZXASCNTXGC-AYMMMOKOSA-N
  • InChI=1/C9H9O/c1-2-8-5-6-9-4-3-7(1)10(8)9/h1-9H/q+1/t7-,8+,9-
    Key: YQBOZXASCNTXGC-AYMMMOKOBA
  • C1=C[C@@H]2[O+]3[C@H]1C=C[C@@H]3C=C2
Properties
C9H9O
Molar mass 133.167
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 coworkers, through a variant of the synthesis that led them to oxatriquinane.[1][2][3]

See also

References

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