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.
See also: prochiral, diastereotopic
PAC, 1996, 68, 2193. 'Basic terminology of stereochemistry (IUPAC Recommendations 1996)' on page 2207 (https://doi.org/10.1351/pac199668122193)