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The nitronium ion (improperly called nitryl ion, because it is not a radical), NO2+ is a generally unstable cation created by the removal of an electron from the paramagnetic nitrogen dioxide molecule, or the protonation of nitric acid.
It is not stable enough to exist in normal conditions, but it is used extensively as an electrophile in the nitration of other substances. The ion is generated in situ for this purpose by mixing sulfuric acid and nitric acid according to the equilibrium:
The nitronium ion also exists in the solid form of dinitrogen pentoxide, N2O5, which is an ionic solid formed from nitronium and nitrate ions. Its liquid and gaseous forms, however, are molecular and do not contain nitronium ions. A few nitronium salts with anions of low nucleophilic power, such as nitronium perchlorate, NO2+ClO4− can be isolated but are extremely reactive.
The nitronium ion is isoelectronic with carbon dioxide and like that compound has a linear structure with a ONO bond angle of 180°.
The compounds nitryl fluoride, NO2F, and nitryl chloride, NO2Cl, are not nitronium salts but rather molecular compounds, as shown by their low boiling points (−72 °C and −6 °C respectively) and short N-X bond lengths (N-F 135 pm, N-Cl 184 pm).
The related negatively charged species is NO2−, the nitrite ion.
Notes and references
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Nitronium_ion". A list of authors is available in Wikipedia.|