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Three aspects of an absolute configuration on the basis of the stereoisogram approach and revised terminology on related stereochemical concepts

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Abstract

A tetrahedral skeleton is considered to belong to the RS-stereoisomeric group denoted by \({\mathbf{T}}_{d{\widetilde{\sigma }}{\widehat{I}}}\). By placing proligands on the four positions of the tetrahedral skeleton, the resulting promolecule is considered to belong to a subgroup of \({\mathbf{T}}_{d\widetilde{\sigma }\widehat{I}}\), where its RS-stereoisomeric properties are illustrated by the corresponding stereoisogram. Three aspects of an absolute configuration, i.e., a chiral aspect, an RS-stereogenic aspect, and a scleral aspect, are formulated on the basis of three attributes of a stereoisogram, i.e., chirality, RS-stereogenicity, and sclerality. The RS-stereodescriptors of the Cahn-Ingold-Prelog (CIP) system are clarified to specify the RS-stereogenic aspect, so that they are assigned to a pair of RS-diastereomers contained in a type-I, type-III, or type-V stereoisogram. To apply the RS-stereodescriptors to the chiral aspect of an absolute configuration, the concept of chirality faithfulness is redefined by proposing odd and even priority permutations.

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Notes

  1. Suppose that a molecule is diastereomeric to a reference molecule. Then, another molecule enantiomeric to the former molecule is also diastereomeric to the reference molecule. This means that a set of diastereomeric molecules contains a pair of enantiomeric molecules.

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  1. Shonan Institute of Chemoinformatics and Mathematical Chemistry, Kaneko 479-7, Ooimachi, Ashigara-Kami-Gun, Kanagawa-Ken, 258-0019, Japan

    Shinsaku Fujita

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  1. Shinsaku Fujita
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Fujita, S. Three aspects of an absolute configuration on the basis of the stereoisogram approach and revised terminology on related stereochemical concepts. J Math Chem 52, 1514–1534 (2014). https://doi.org/10.1007/s10910-014-0326-0

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