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Concept
Oxonium ion
Summary
In chemistry, an oxonium ion is any cation containing an oxygen atom that has three bonds and 1+ formal charge. The simplest oxonium ion is the hydronium ion ().
Hydronium is one of a series of oxonium ions with the formula RnH3−nO+.
Oxygen is usually pyramidal with an sp3 hybridization. Those with n = 1 are called primary oxonium ions, an example being protonated alcohol (e.g. methanol). In acidic media, the oxonium functional group produced by protonating an alcohol can be a leaving group in the E2 elimination reaction. The product is an alkene. Extreme acidity, heat, and dehydrating conditions are usually required. Other hydrocarbon oxonium ions are formed by protonation or alkylation of alcohols or ethers (R−C−−R1R2).
Secondary oxonium ions have the formula R2OH+, an example being protonated ethers.
Tertiary oxonium ions have the formula R3O+, an example being trimethyloxonium. Tertiary alkyloxonium salts are useful alkylating agents. For example, triethyloxonium tetrafluoroborate (Et3O+)(BF4-), a white crystalline solid, can be used, for example, to produce ethyl esters when the conditions of traditional Fischer esterification are unsuitable. It is also used for preparation of enol ethers and related functional groups.
Oxatriquinane and oxatriquinacene are unusually stable oxonium ions, first described in 2008. Oxatriquinane does not react with boiling water or with alcohols, thiols, halide ions, or amines, although it does react with stronger nucleophiles such as hydroxide, cyanide, and azide.
Another class of oxonium ions encountered in organic chemistry is the oxocarbenium ions, obtained by protonation or alkylation of a carbonyl group e.g. R−C=−R′ which forms a resonance structure with the fully-fledged carbocation R−−O−R′ and is therefore especially stable:
An unusually stable oxonium species is the gold complex tris[triphenylphosphinegold(I)]oxonium tetrafluoroborate, [(Ph3PAu)3O][BF4], where the intramolecular aurophilic interactions between the gold atoms are believed responsible for the stabilisation of the cation.
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