Oxatriquinacene is an
organic
Organic may refer to:
* Organic, of or relating to an organism, a living entity
* Organic, of or relating to an anatomical organ
Chemistry
* Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...
cation
An ion () is an atom or molecule with a net electrical charge.
The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...
with formula . It is an
oxonium ion, with a trivalent
oxygen atom with +1
charge connected to
carbons
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon makes up o ...
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
Oxatriquinane (oxoniaperhydrotriquinacene) is an alkyl oxonium ion with formula (CH2CH2CH)3O+. It has a cyclononane backbone, with a trivalent oxygen connected to carbon 1, 4, and 7, forming three fused pentagonal rings. In contrast to most trial ...
. It reacts with water, but can be dissolved in
acetonitrile
Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not clas ...
. It is of interest as a possible precursor to
oxaacepentalene, a hypothetical neutral aromatic species.
[
Oxatriquinacene was obtained in 2008 by Mascal and coworkers, through a variant of the synthesis that led them to oxatriquinane.][
][
]
See also
* Triethyloxonium tetrafluoroborate
* Brookhart's acid
Brookhart's acid is the salt of the diethyl ether oxonium ion and tetrakis ,5-bis(trifluoromethyl)phenylorate (BAr′4). It is a colorless solid, used as a strong acid. The compound was first reported by Volpe, Grant, and Brookhart in 1992.
Pr ...
* Pyrylium salt
References
{{reflist
Heterocyclic compounds with 3 rings
Oxygen heterocycles
Oxonium compounds