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enantiotopic

Constitutionally identical atoms or groups in molecules which are related by symmetry elements of the second kind only (mirror plane, inversion centre or rotation–reflection axis). For example the two groups c in a grouping Cabcc are enantiotopic. Replacement of one of a pair of enantiotopic groups forms one of a pair of enantiomers. Analogously, if complexation or addition to one of the two faces defined by a double bond or other molecular plane gives rise to a chiral species, the two faces are called enantiotopic.
Source:
PAC, 1996, 68, 2193 (Basic terminology of stereochemistry (IUPAC Recommendations 1996)) on page 2207
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IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.E02083.
Original PDF version: http://www.iupac.org/goldbook/E02083.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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