Impact of long-range van der Waals forces on chiral recognition in a Cinchona alkaloid chiral selector system
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F13%3A10159276" target="_blank" >RIV/00216208:11310/13:10159276 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15310/13:33147302
Result on the web
<a href="http://dx.doi.org/10.1039/c3cp44444a" target="_blank" >http://dx.doi.org/10.1039/c3cp44444a</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c3cp44444a" target="_blank" >10.1039/c3cp44444a</a>
Alternative languages
Result language
angličtina
Original language name
Impact of long-range van der Waals forces on chiral recognition in a Cinchona alkaloid chiral selector system
Original language description
Singly-charged complexes of (8S, 9R)-tert-butylcarbamoylquinine (tBuCQN), N-3,5-dinitrobenzoyl-(S, R)-leucine (DNB-S/R-leucine), and alkali metal counter ions (Li+, Na+, K+) were investigated by density-functional theory. It is shown that the cations prefer formation of an ionic pair with the carboxylate group of DNB-Leu over the formation of a cation-pi interaction. The [tBuCQN center dot DNB-S/R-Leu center dot Na](+) complex is bound by a Coulombic attraction, a hydrogen bond, a pi - pi interaction and van der Waals forces. The tBuCQN chiral selector preferentially complexes with the DNB-S-Leu enantiomer, because the favourable stereochemistry allows the stabilization of the complex by at least one binding mode more compared to the complex containingthe DNB-R-Leu molecule. Weakening of the binding modes is observed using the lithium counter ion compared to the sodium one. The weakening is more pronounced in [tBuCQN center dot DNB-R-Leu center dot Li](+) than in [tBuCQN center dot DN
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Physical Chemistry Chemical Physics
ISSN
1463-9076
e-ISSN
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Volume of the periodical
15
Issue of the periodical within the volume
16
Country of publishing house
US - UNITED STATES
Number of pages
9
Pages from-to
6113-6121
UT code for WoS article
000316803500043
EID of the result in the Scopus database
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