Oxonium ion

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Oxonium ion

The oxonium ion in chemistry

Chemistry

Chemistry is the science concerned with the composition, structure, and properties of matter, as well as the changes it undergoes during chemical reactions....
is any positive oxygen

Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
cation, which has three bonds

Chemical bond

A chemical bond is the physical process responsible for the attractive interactions between atoms and molecules, and that which confers stability to diatomic and polyatomic chemical compounds....
. The simplest oxonium ion is the hydronium

Hydronium

In chemistry, hydronium is the common name for the aqueous cation hydrogen3oxygen+ derived from protonation of water. It is the simplest type of an oxonium ion....
ion H₃O⁺. Another oxonium ion frequently encountered in organic chemistry

Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
is obtained by protonation or alkylation of a carbonyl

Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
group e.g. R-C=O⁺-R' which forms a resonance structure with the fully fledged carbocation

Carbocation

A carbocation is an ion with a positively-charged carbon atom. The charged carbon atom in a carbocation is a "sextet", i.e. it has only six electrons in its outer Electron shell#Valence shell instead of the eight valence electrons that ensures maximum stability ....
R-C⁺-O-R' and is therefore especially stable:

Stable alkyloxonium salts exist; they are extensively used as alkylating agents.

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Encyclopedia

The oxonium ion in chemistry

Chemistry

Chemistry is the science concerned with the composition, structure, and properties of matter, as well as the changes it undergoes during chemical reactions....
is any positive oxygen

Oxygen

Chemical bond

Hydronium

Organic chemistry

Carbonyl

Carbocation

Stable alkyloxonium salts exist; they are extensively used as alkylating agents. For example, triethyloxonium tetrafluoroborate (Et₃O⁺)(BF₄^-) is a white crystalline solid. It is a powerful ethylating agent. It can be used, for example, to produce ethyl esters when the conditions of traditional Fischer esterification

Esterification

Esterification is the general name for a chemical reaction in which two reactants form an ester as the product . Esters are common in organic chemistry and biological materials, and often have a characteristic pleasant, fruity odor....
are unsuitable.


general pyramidal oxonium ion	skeletal formula Skeletal formula The skeletal formula of an organic compound is a shorthand representation of its molecular geometry. Skeletal formulae are ubiquitous in organic chemistry because they show complicated structures clearly and they are quick and simple to draw.... of the trimethyloxonium cation	ball-and-stick model Ball-and-stick model Ball-and-stick models and space-filling models are three-dimensional space or spatial molecular models which serve to display the structure of chemical products and chemical substance or biomolecules.... of trimethyloxonium	space-filling model Space-filling model Space-filling models , like ball-and-stick models, belong to the Three dimensional space or spatial molecular models, which serve to display the structure of chemical products and substances or biomolecules.... of trimethyloxonium

Other hydrocarbon oxonium ions are formed by protonation or alkylation of alcohol

Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s e.g. R-C-O⁺-R¹R². In acidic media, the oxonium functional group

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
produced by protonating an alcohol can be a leaving group

Leaving group

A leaving group in chemistry is an ion or substituent with the ability to detach itself from a molecule. The remaining molecule or fragment remaining is known as the residual or main part....
in the E2 elimination

Elimination reaction

An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism ....
reaction, because when it receives an electron, it becomes a water

Water

Water is a common chemical substance that is essential for the survival of all known forms of life. In typical usage, water refers only to its liquid form or States of matter, but the substance also has a solid state, ice, and a gaseous state, water vapor or steam....
molecule. The product is an alkene

Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
. Extreme acidity, heat and dehydrating conditions are usually required.

Oxatriquinane

Oxatriquinane

Oxatriquinane is an alkyl oxonium ion, remarkable for being stable in aqueous solution. Oxonium ions normally are strong alkylating agents and are only observed in solution as reactive intermediates or under extreme conditions....
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.

Oxonium ion

See also