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Nitrenium ion

A nitrenium ion (also called: aminylium ion) in organic chemistry is a reactive intermediate based on nitrogen with both an electron lone pair and a positive charge and with two substituents (R₂N⁺) ^[1]. The compound can have both a singlet and a triplet state.

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Aryl nitrenium ions are currently investigated because of their involvement in certain DNA damaging processes. These intermediates can have microsecond or longer lifetimes in water ^[2].

Nitrenium ions are also intermediates in organic reactions for instance the Bamberger rearrangement. They can also act as electrophiles in electrophilic aromatic substitution ^[3].

The term imidonium ion with the same meaning is now obsolete.

References

^ Gold Book definition link
^ Reaction of Aromatic Azides with Strong Acids: Formation of Fused Nitrogen Heterocycles and Arylamines Marcia de Carvalho, Ana E.P.M. Sorrilha, and J. Augusto R. Rodrigues J. Braz. Chem. Soc., Vol. 10, No. 5, 415-420, 1999. link
^ Microwave-assisted generation of carbazolyl nitrenium cation Dariusz Bogdal ARKIVOC 2001 (vi) 109-115 Link