04146 IUPAC Gold Book - nitrenium ions 10.1351/goldbook.N04146 N04146 current synonyms: aminylium ions, imidonium ions, imin, imine radical 1 The cation ($\ce{H2N{:}^{+}}$) and its N-hydrocarbyl derivatives ($\ce{R2N{:}^{+}}$), in which the nitrogen has a positive charge, and two unshared electrons. A synonymous but less widely used term is aminylium ions. The alkylidene derivatives of ($\ce{H2N{:}^{+}}$), ($\ce{R2C=N{:}^{+}}$), still belong to the class nitrenium ions, but are more precisely designated by the term iminylium ions. cation https://goldbook.iupac.org/terms/view/C00907 iminylium ions https://goldbook.iupac.org/terms/view/I02964 PAC, 1995, 67, 1307. 'Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)' on page 1350 (https://doi.org/10.1351/pac199567081307) PAC, 1994, 66, 1077. 'Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)' on page 1145 (https://doi.org/10.1351/pac199466051077) https://goldbook.iupac.org/terms/view/N04146/html https://goldbook.iupac.org/terms/view/N04146/json https://goldbook.iupac.org/terms/view/N04146/plain Citation: 'nitrenium ions' in IUPAC Compendium of Chemical Terminology, 5th ed. International Union of Pure and Applied Chemistry; 2025. Online version 5.0.0, 2025. 10.1351/goldbook.N04146 The IUPAC Gold Book is licensed under Creative Commons Attribution-ShareAlike CC BY-SA 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) for individual terms. If you are interested in licensing the Gold Book for commercial use, please contact the IUPAC Executive Director at executivedirector@iupac.org . The International Union of Pure and Applied Chemistry (IUPAC) is continuously reviewing and, where needed, updating terms in the Compendium of Chemical Terminology (the IUPAC Gold Book). Users of these terms are encouraged to include the version of a term with its use and to check regularly for updates to term definitions that you are using. 2026-07-24T13:18:18+00:00