N-Oxoammonium salt

The structure of a typical N-oxoammonium salt.

N-Oxoammonium salts in organic chemistry are a class of organic compounds sharing a functional group with the general structure R₁R₂N⁺=O X⁻ where X⁻ is the counterion. They are isoelectronic with carbonyls and structurally related to aldoximes (hydroxylamines) and aminoxyl (nitroxide) radicals, with which they can interconvert via a series of redox steps.

The N-oxoammonium salts are used for oxidation of alcohols to carbonyl groups, as well as other forms of oxoammonium-catalyzed oxidations. The stable radical TEMPO reacts via its N-oxoammonium salt.

See also

• Nitrone – structurally related, the N-oxide of an imine