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For double bonded molecules, Cahn–Ingold–Prelog priority rules (CIP rules) are followed to determine the priority of substituents of the double bond. If both of the high priority groups are on the same side of the double bond (cis configuration), then the stereoisomer is assigned the configuration Z (zusammen, German word meaning "together").
The designations are based on the same Cahn–Ingold–Prelog priority rules used for tetrahedral stereocenters. [3] The chiral axis is viewed end-on and the two "near" and two "far" substituents on the axial unit are ranked, but with the additional rule that the two near substituents have higher priority than the far ones. [4]
Absolute configuration uses a set of rules to describe the relative positions of each bond around the chiral center atom. The most common labeling method uses the descriptors R or S and is based on the Cahn–Ingold–Prelog priority rules. R and S refer to rectus and sinister, Latin for right and left, respectively.
Cahn–Ingold–Prelog priority rules are part of a system for describing a molecule's stereochemistry. They rank the atoms around a stereocenter in a standard way, allowing unambiguous descriptions of their relative positions in the molecule.
Alternately, all four groups can be ranked by Cahn–Ingold–Prelog priority rules, with overall priority given to the two groups on the "front" atom of the Newman projection. The two configurations determined in this way are termed R a and S a, in analogy to the traditional R/S for a traditional tetrahedral stereocenter. [12]
The Cahn-Ingold-Prelog (CIP) system uses R and S designations to define the configuration of atoms about any stereocenter. [7] A designation of R denotes a clockwise direction of substituent priority around the stereocenter, while a designation of S denotes a counter-clockwise direction of substituent priority. [7]
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In general the D/L system of nomenclature is superseded by the Cahn-Ingold-Prelog (CIP) rule to describe the configuration of a stereogenic/chiral center. In the CIP or R/S convention, or sequence rule, the configuration, spatial arrangements of ligands/substituents around a chiral center, is labeled as either "R" or "S".