Nitrenium ion
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3D model (
JSmol ) |
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ChEBI | |
ChemSpider | |
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Properties | |
H2N+ | |
Molar mass | 16.022 g·mol−1 |
Related compounds | |
Related compounds
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NH4+; NH2−; N•H2 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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A nitrenium ion (also called: aminylium ion or imidonium ion (obsolete)) in
Aryl nitrenium ions are of biological interest because of their involvement in certain DNA damaging processes. They are generated upon in vivo oxidation of arylamines. The regiochemistry and energetics of the reaction of phenylnitrenium ion with guanine has been investigated using density functional theory computations.[4]
Nitrenium species have been exploited as intermediates in organic reactions.[5] They are typically generated via heterolysis of N–X (X = N, O, Halogen) bonds. For instance, they are formed upon treatment of chloramine derivatives with silver salts or by activation of aryl hydroxylamine derivatives or aryl azides with Brønsted or Lewis acids.[6] The Bamberger rearrangement is an early example of a reaction that is now thought to proceed via an aryl nitrenium intermediate. They can also act as electrophiles in electrophilic aromatic substitution.[7]
See also
- The related neutral nitrenes R–N:
References
- ISBN 9780471233244.[page needed]
- .
- PMID 11749633.
- S2CID 250845065.
- ISSN 0385-5414.)
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: CS1 maint: DOI inactive as of March 2024 (link - .