The Cahn, Ingold and Prelog System: eliminating ambiguity in the comparison of diastereomorphic and enantiomorphic ligands

The Cahn, Ingold and Prelog (CIP) system is an essential tool in organic chemistry nomenclature for the specification of stereogenic units. However, over the years, examples of molecules for which such specification was found impossible, ambiguous or inconsistent, have steadily accumulated. Herein, a simple methodology for the comparison of combinations of chiral units, namely to evaluate if two ligands are diastereomorphic, enantiomorphic or identical, is proposed, based on a reference descriptor not linked to a digraph node.

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