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Chirality descriptors for so-called planar-chiral molecules are generally defined by ad hoc sequence rules that depend upon the nature of the considered molecule. The authors would like to point out that despite the sustained efforts of the IUPAC to unify both the terminology of stereochemistry and the nomenclature of chiral molecules, two definitions of chirality descriptors for metallocenic planar-chirality, which are based on different perceptions of planar-chirality itself, still coexist and can be found in the literature. The first one is based on Schlögl's first nomenclature, which was proposed in 1964 in two consecutive reports; it is based on the determination of the succession of the aromatic ring's substituents (either clockwise (R) or anti-clockwise S, by order of decreasing priority, as the molecule is observed from its principal axis perpendicularly to the aromatic ligand's plane, the π-bonded metal sitting underneath the plane. The second one is an exten
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Chirality descriptors for so-called planar-chiral molecules are generally defined by ad hoc sequence rules that depend upon the nature of the considered molecule. The authors would like to point out that despite the sustained efforts of the IUPAC to unify both the terminology of stereochemistry and the nomenclature of chiral molecules, two definitions of chirality descriptors for metallocenic planar-chirality, which are based on different perceptions of planar-chirality itself, still coexist and can be found in the literature. The first one is based on Schlögl's first nomenclature, which was proposed in 1964 in two consecutive reports; it is based on the determination of the succession of the aromatic ring's substituents (either clockwise (R) or anti-clockwise (S)), by order of decreasing priority, as the molecule is observed from its principal axis perpendicularly to the aromatic ligand's plane, the π-bonded metal sitting underneath the plane. The second one is an extension of the Cahn-Ingold-Prelog (abbreviated CIP) priority, or sequence, rule proposed in 1967 again by Schlögl, who recommended it in place of his first nomenclature: "We shall therefore in the future make use of the nomenclature proposed by Cahn, Ingold and Prelog...". Throughout the present article this extended CIP sequence rule is used to assign the pS or the pR stereochemical descriptors to planar chiral molecules. Readers are referred to the following references for more details: (a) Schlögl, K.; Fried, M. Monatsh. Chem. 1964, 95, 558-575.
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