Format:
Online-Ressource
ISSN:
1099-0690
Content:
Abstract: Two new receptors, a cavitand–salen (2) and a uranyl–cavitand–salen (3), for the selective molecular recognition of chiral ammonium ion pairs, where the amino acid is the countercation or counteranion of the ion pair, were designed and synthesized. UV/Vis measurements indicate the formation of 1:1 host–guest complexes with high association constants and good to excellent enantiomeric discriminations. NMR spectroscopic experiments confirmed cation–π interactions between the organic cations and the π‐electron‐rich cavity, leading to the stability of the complexes, as well as the coordination of the amino acid carboxylate anion to the uranyl metal center. Extraction experiments showed that a racemic mixture of (R,S)‐α‐methylbenzyltrimethylammonium iodides undergoes chiral resolution by 2 with high selectivity.
In:
volume:2011
In:
number:28
In:
year:2011
In:
pages:5674-5680
In:
extent:7
In:
European journal of organic chemistry, Weinheim : Wiley-VCH Verl., 1998-, 2011, Heft 28 (2011), 5674-5680 (gesamt 7), 1099-0690
Language:
English
DOI:
10.1002/ejoc.201100955
URN:
urn:nbn:de:101:1-2023032106193993016000
URL:
https://doi.org/10.1002/ejoc.201100955
URL:
https://nbn-resolving.org/urn:nbn:de:101:1-2023032106193993016000
URL:
https://d-nb.info/1283937409/34
URL:
https://doi.org/10.1002/ejoc.201100955
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