Symmetry-Itemized Enumeration of Quadruplets of RS-Stereoisomers Derived from a Trigonal Pyramidal Skeleton

• Fujita Shinsaku

  Shonan Institute of Chemoinformatics and Mathematical Chemistry

書誌事項

タイトル別名

• Symmetry-Itemized Enumeration of Quadruplets of <i>RS</i>-Stereoisomers Derived from a Trigonal Pyramidal Skeleton

抄録

Stereoisograms of five types are devised as graphical expressions of the action of an RS-stereoisomeric group on a trigonal pyramidal skeleton. A quadruplet of promolecules (i.e., a reference promolecule, its enantiomer, its RS-diastereomer, and its holantimer) contained in a stereoisogram is counted once as an equivalence class under the action of an RS-stereoisomeric group. An RS-stereoisomeric group <img align="middle" src="./Graphics/abst-20150015-1.gif"/> is constructed by starting from the point group C_3v of a trigonal pyramidal skeleton, where a point group C_3v, an RS-permutation group <img align="middle" src="./Graphics/abst-20150015-2.gif"/>, a ligand-reflection group C_3Î are integrated. Fujita’s unit-subduced-cycle-index (USCI) approach for enumeration under point groups is extended to cover enumeration under RS-stereoisomeric groups. The fixed-point-matrix (FPM) method and the partial-cycle-index (PCI) method of the USCI approach are applied to symmetry-itemized and type-itemized enumeration of quadruplets of promolecules under the action of the RS-stereoisomeric group <img align="middle" src="./Graphics/abst-20150015-1.gif"/>. Theoretical foundations of stereochemical nomenclature are discussed on the basis of Fujita’s stereoisogram approach, where three aspects of absolute configuration are emphasized. Prochirality and pro-RS-stereogenicity are clarified to be conceptually distinct, just as chirality and RS-stereogenicity are conceptually distinct. Young’s tableaux for (pro)chirality and those for (pro-)RS-stereogenicity are compared to demonstrate such conceptual distinctions. It follows that a pair of R/S-stereodescriptors is assigned on the basis of RS-stereogenicity, not of chirality; and a pair of pro-R/pro-S-descriptors is assigned on the basis of pro-RS-stereogenicity, not of prochirality.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 88 (9), 1265-1283, 2015

  公益社団法人 日本化学会

キーワード

• General Chemistry

詳細情報

• CRID: 1390001204144274944
• NII論文ID: 130005099095
• NII書誌ID: AA00580132
• DOI: 10.1246/bcsj.20150015
• ISSN: 13480634
• ISSN: 00092673
• NDL書誌ID: 026736057
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I026736057
• Web Site: https://academic.oup.com/bcsj/article-pdf/88/9/1265/56278278/bcsj.20150015.pdf
• 本文言語コード: en
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