Term: nitrile ylides https://doi.org/10.1351/goldbook.N04153 Definition: 1,3-dipolar compounds having the structure: N04153-1.png The uncharged canonical form N04153-2.png is called an alkylidene- (or hydrocarbylidene-) amino carbene; the name iminyl carbene is incorrect because iminyl is not a recognized prefix for –N=CR2. Related Terms: 1) carbenes (http://doi.org/10.1351/goldbook.C00806). 2) dipolar compounds (http://doi.org/10.1351/goldbook.D01753). 3) canonical form (http://doi.org/10.1351/goldbook.C01309). Images: 1) Not defined (https://goldbook.iupac.org/img/inline/N04153-1.png) 2) Not defined (https://goldbook.iupac.org/img/inline/N04153-2.png) Source: PAC, 1995, 67, 1307. 'Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)' on page 1351 (https://doi.org/10.1351/pac199567081307) Citation: 'nitrile ylides' in IUPAC Compendium of Chemical Terminology, 5th ed. International Union of Pure and Applied Chemistry; 2025. Online version 5.0.0, 2025. https://doi.org/10.1351/goldbook.N04153 License: 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. Disclaimer: 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.