Journal Article10.1002/ANIE.198205671
Basic Principles of the CIP-System and Proposals for a Revision†
Vladlmir Prelog,Günter Helmchen +1 more
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TL;DR: From Configurational Notation of Stereoisomers to the Conceptual Basis of Stereo Chemistry as mentioned in this paper is the title of a lecture [V. Prelog, ACS Symp. Ser. No. 12 (1975) 179] in which the chronologically and alphabetically third member of the CIP-triumvirate discusses the history of the system.
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Abstract: “From Configurational Notation of Stereoisomers to the Conceptual Basis of Stereochemistry” is the title of a lecture [V. Prelog, ACS Symp. Ser. No. 12 (1975) 179] in which the chronologically and alphabetically third member of the CIP-triumvirate discusses the history of the CIP-system. The experience accumulated in the meantime, particularly the efforts to teach computers to use the system as described in 1966 by Cahn, Ingold and Prelog, has shown that certain of its aspects must be more strictly formulated and others modified. Questions dealing with stereoisomers (and stereotopicity), which previously have been treated predominantly in a pragmatic manner, are now discussed in a systematic way.
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Citations
Chiral Atropisomeric Indenocorannulene Bowls: Critique of the Cahn-Ingold-Prelog Conception of Molecular Chirality
Yujia Wang,Oliver Allemann,T. Silviu Balaban,Nicolas Vanthuyne,Anthony Linden,Kim K. Baldridge,Jay S. Siegel +6 more
TL;DR: These studies bring into question any systematic assignment of nontrivial stereoelements and refute any assertion of congruence between "Cahn-Ingold-Prelog elements" and the physical or "Cartesian" basis of chirality.
Internal chirality descriptors iR and iS and ire and isi. A proposed notation to extend the usefulness of the R/S system by retaining the sense of stereochemistry in cases of ligand ranking changes.
TL;DR: The proposed iR/iS notation could find profitable use in comparative studies where there is a need to avoid confusion arising from changing assignments due to priority rules or to expedite the ease of comprehension.
A brief review of Cn-symmetric calixarenes and resorcinarenes
TL;DR: The addition of chirality to these non-planar molecules is an exciting enhancement of their already robust potential, offering much promise as ligands for chiral catalysis and enantioselective separations.
Supramolecular Chirality in Coordination Chemistry
Georg Seeber,Bryan E. F. Tiedemann,Kenneth N. Raymond +2 more
TL;DR: This chapter explores supramolecular chirality in coordination chemistry, focusing on chiral architectures formed from achiral units via metal coordination, with emphasis on assemblies with chiral cavities for guest encapsulation and potential applications in recognition, storage, and nano-reaction vessels.
References
Specification of Molecular Chirality
TL;DR: In this article, the topological analysis of chiral molecular models has been extended to deal with organic-chemical conformations, and, on the other hand, with inorganic-chemical configurations to ligancy six.
1.7K
Description of steric relationships across single bonds
W. Klyne,Vladimir Prelog +1 more
TL;DR: In this article, the authors propose an approach to bezeichnungen fur partielle Konformationen (Konstellationen) abgeleitet.
661
Unusually High Barriers to Rotation Involving the Tetrahedral Carbon Atom
TL;DR: In this article, the authors considered derivatives of triptycene and fluorene whose barriers to rotation were of the order of 30 kcal/mol, and showed that the barrier to rotation is high enough to give rise to rotamers.
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