A nitronium ion is a positively charged ion with the chemical formula NO2+. It is a strong oxidizing agent and an electrophile that is used in the nitration of other substances:
Properties
A nitronium ion is a linear molecule that is isoelectronic with carbon dioxide. It is an onium ion, similar to ammonium, because its nitrogen atom has a +1 charge.
Formation
A nitronium ion can be created by removing an electron from a nitrogen dioxide molecule or by protonating nitric acid. It is also the active agent in fuming nitric acid, which is a mixture of sulfuric and nitric acids.
Reactions
A nitronium ion acts as an electrophile in reactions with aromatic compounds, forming a positively charged complex. It is also used in the oxidative functionalization of carbon-heteroatom bonds.
Applications
A nitronium ion is used in a number of applications, including the pinacol-pinacolone rearrangement, the oxidative displacement of alkyl halides, and the oxidative fluorination of thioethers and dithiolanes.
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