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.

See also

• The related neutral nitrenes R-N

References