Stereogenicity Revisited. Proposal of Holantimers for Comprehending the Relationship between Stereogenicity and Chirality

Journal of Organic Chemistry

Volumn 69, Issue 9, 2004, Pages 3158-3165

  Fujita, Shinsaku ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; CORRELATION METHODS; MATHEMATICAL MODELS; MOLECULAR DYNAMICS;

CHIRALITY; STEREOGENICTY; STEREOISOGRAMS;

STEREOCHEMISTRY;

INORGANIC COMPOUND; ORGANIC COMPOUND;

ARTICLE; CHIRALITY; COMPLEX FORMATION; CONCEPT FORMATION; CORRELATION ANALYSIS; ENANTIOMER; HOLANTIMER; ISOMER; NOMENCLATURE; STEREOCHEMISTRY; STEREOGENICITY; STEREOISOGRAM; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 2142717364     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030393v     Document Type: Article

References (25)

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18. Fujita, S. Symmetry and Combinatorial Enumeration in Chemistry; Springer-Verlag: Berlin-Heidelberg, 1991.
19. Fujita, S. J. Math. Chem. 2003, 33, 113-143.
20. The terms "holantimer" and "holantimeric" are coined by Greek words "holo" and "anti", where the "holo" or "hol" represents "whole" and "entire" and the "anti" represents "opposite to". It should be noted that each ligand may be achiral, where the resulting ligand is superimposable to the original one.
21. Fujita, S. Tetrahedron 1991, 47, 31-46.
22. 3 in tetramethylmethane is replaced by a proligand A, the rees not undergo such an eventual restriction as described above.
23. The term "stereoisogram" is coined by combining the words "stereoisomer" and "isogram" of Greek origin in order to designate a quartet of stereoisomers for clarifying the relationship between chirality and stereogenicity.
24. Strictly speaking, the pair of enantiomers (1 and 2) in each row can be regarded as being diastereomeric from the viewpoint of RS-stereogenicity. In other words, the enantiomeric relationship and the diastereomeric one occasionally overlap each other in type I.
25. The term "astereogenic" is used in place of the term "nonstereogenic", though the latter has been used rather commonly. The usage of the former term is to emphasize that the present approach based on group theory19 has rigorously defined "stereogenic groups" and "astereogenic groups", which have not been involved in the conventional usage of the term "nonstereogenic". The terms "RS-stereogenic" and "RS-astereogenic" are coined here to differentiate them from the terms "stereogenic/astereogenic".