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Chirality
Article . 2004 . Peer-reviewed
License: Wiley Online Library User Agreement
Data sources: Crossref
Chirality
Article . 2004
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Crystal and molecular structures of new enantiopure quinuclidines

Authors: Kania, Iwona; Stadnicka, Katarzyna; Oleksyn, Barbara;

Crystal and molecular structures of new enantiopure quinuclidines

Abstract

AbstractX‐ray crystal structure analysis was performed on single crystals of two diastereomeric enantiopure quinuclidines, (3R,8R)‐3‐vinyl‐8‐hydroxymethyl‐quinuclidine (quincoridine, QCD) and (3R,8S)‐3‐vinyl‐8‐hydroxymethyl‐quinuclidine (quincorine, QCI) as their salts with tartaric and p‐toluenesulphonate anions, respectively. The molecules of these quinuclidine derivatives are considered here as fragments of the Cinchona alkaloids, quinidine and quinine. A comparison of the conformational features of QCD, QCI, and Cinchona alkaloids in the crystalline state shows that the molecular geometry of the title compounds is similar to that of threo‐alkaloids (e.g., R,R isomer of epicinchonine) rather than to quinidine and quinine. The packing of the molecules in both structures is dominated by intermolecular hydrogen bonds. Chirality 16:180–189, 2004. © 2004 Wiley‐Liss, Inc.

Country
Poland
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Keywords

conformation, absolute configuration, Cinchona alkaloids, hydrogen bonds, chirality, X-ray structure analysis

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
5
Average
Average
Top 10%
Green