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.
PAC, 1996, 68, 2193
(Basic terminology of stereochemistry (IUPAC Recommendations 1996))
on page 2207
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. https://doi.org/10.1351/goldbook