کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1345084 1500345 2014 21 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Stereoisograms for reorganizing the theoretical foundations of stereochemistry and stereoisomerism. Part 2: rational avoidance of misleading standpoints for R/S-stereodescriptors of the Cahn–Ingold–Prelog system
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Stereoisograms for reorganizing the theoretical foundations of stereochemistry and stereoisomerism. Part 2: rational avoidance of misleading standpoints for R/S-stereodescriptors of the Cahn–Ingold–Prelog system
چکیده انگلیسی

The stereoisogram approach presupposes three distinct pairs of attributes, that is, chirality/achirality, RS-stereogenicity/RS-astereogenicity, and sclerality/asclerality, which are integrated into RS-stereoisomerism represented by stereoisograms. The mathematical rationalization of the three pairs of attributes is in sharp contrast to the presumption of a single pair of attributes (i.e., chirality/achirality) supporting modern stereochemistry. Thus, a pair of R/S-stereodescriptors of the Cahn–Ingold–Prelog (CIP) system is clarified to be assigned to a pair of RS-diastereomers, not to a pair of enantiomers. In particular, the ‘units’ of the CIP system (e.g., ‘chirality units’, ‘stereogenic units’, and ‘pseudoasymmetric units’) are replaced by promolecules having type-I, type-III, or type-V stereoisograms; the ‘chirality rule’ of the CIP system is replaced by the RS-stereogenicity rule of the stereoisogram approach; as well as the use of ‘reflection invariance’ for ‘pseudoasymmetric units’ being avoided by developing the concept of chirality faithfulness/unfaithfulness. Global and local symmetries are discussed in terms of correlation diagrams of stereoisograms.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 25, Issues 16–17, 15 September 2014, Pages 1169–1189
نویسندگان
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