Term: chirality axis https://doi.org/10.1351/goldbook.C01059 Definition: An axis about which a set of ligands is held so that it results in a spatial arrangement which is not superposable on its mirror image. For example with an allene abC=C=Ccd the chiral axis is defined by the C=C=C bonds; and with an ortho-substituted biphenyl the atoms C-1, C-1', C-4 and C-4' lie on the chiral axis. Related Terms: 1) ligands (http://doi.org/10.1351/goldbook.L03518). 2) chiral (http://doi.org/10.1351/goldbook.C01057). Source: PAC, 1996, 68, 2193. 'Basic terminology of stereochemistry (IUPAC Recommendations 1996)' on page 2203 (https://doi.org/10.1351/pac199668122193) Citation: 'chirality axis' 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.C01059 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.