Title: organometallic compounds
Long Title: IUPAC Gold Book - organometallic compounds
DOI: 10.1351/goldbook.O04328
Status: current

Definition
Classically compounds having bonds between one or more metal atoms and one or more carbon atoms of an organyl group. Organometallic compounds are classified by prefixing the metal with organo-, e.g. organopalladium compounds. In addition to the traditional metals and semimetals, elements such as boron, silicon, arsenic and selenium are considered to form organometallic compounds, e.g. organomagnesium compounds $\ce{MeMgI}$ iodo(methyl)magnesium, $\ce{Et2Mg}$ diethylmagnesium; an organolithium compound $\ce{BuLi}$ butyllithium; an organozinc compound $\ce{ClZnCH2C(=O)OEt}$ chloro(ethoxycarbonylmethyl)zinc; an organocuprate $\ce{Li^{+}[CuMe2]^{−}}$ lithium dimethylcuprate; an organoborane $\ce{Et3B}$ triethylborane. The status of compounds in which the canonical anion has a delocalized structure in which the negative charge is shared with an atom more electronegative than carbon, as in enolates, may vary with the nature of the anionic moiety, the metal ion, and possibly the medium; in the absence of direct structural evidence for a carbon–metal bond, such compounds are not considered to be organometallic.

Related Terms
- Grignard reagents: https://goldbook.iupac.org//terms/view/G02699
- acetylides: https://goldbook.iupac.org//terms/view/A00067
- anion: https://goldbook.iupac.org//terms/view/A00358
- enolates: https://goldbook.iupac.org//terms/view/E02123
- ferrocenophanes: https://goldbook.iupac.org//terms/view/F02345
- metallocenes: https://goldbook.iupac.org//terms/view/M03865
- moiety: https://goldbook.iupac.org//terms/view/M03968

Source
- PAC, 1995, 67, 1307. 'Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)' on page 1353 (https://doi.org/10.1351/pac199567081307)

Other Outputs
- html: https://goldbook.iupac.org/terms/view/O04328/html
- json: https://goldbook.iupac.org/terms/view/O04328/json
- xml: https://goldbook.iupac.org/terms/view/O04328/xml

Citation: Citation: 'organometallic compounds' 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.O04328
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.
Collection: If you are interested in licensing the Gold Book for commercial use, please contact the IUPAC Executive Director at executivedirector@iupac.org .
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.
Accessed: 2026-06-20T12:22:14+00:00