Mechanistic considerations of enantiorecognition on novel Cinchona alkaloid-based zwitterionic chiral stationary phases from the aspect of the separation of trans-paroxetine enantiomers as model compounds
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F16%3A43902790" target="_blank" >RIV/60461373:22310/16:43902790 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1016/j.jpba.2016.02.043" target="_blank" >http://dx.doi.org/10.1016/j.jpba.2016.02.043</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.jpba.2016.02.043" target="_blank" >10.1016/j.jpba.2016.02.043</a>
Alternative languages
Result language
angličtina
Original language name
Mechanistic considerations of enantiorecognition on novel Cinchona alkaloid-based zwitterionic chiral stationary phases from the aspect of the separation of trans-paroxetine enantiomers as model compounds
Original language description
The enantiomers of trans-paroxetine were separated on four chiral stationary phases (CSPs) based on chiral zwitterionic Cinchona alkaloids fused with (R,R)- or (S,S)-trans-2-aminocyclohexanesulfonic acid. The enantioseparations were carried out in polar-ionic or in hydro-organic mobile phases with MeOH/THF, Meal/THF, Meal/THF/H2O and MeOH/MeCN/THF containing organic acid and base additives, in the temperature range 0-50 degrees C. The effects of the mobile phase composition, the natures and concentrations of the additives and temperature on the separations were investigated. Thermodynamic parameters were calculated from plots of In alpha vs 1/T. Delta(Delta H degrees) ranged between -3.0 and +1.5 kJ mol(-1), and Delta(Delta S degrees) between -8.8 and +5.9 J mol(-1) K-1. The enantioseparation was generally enthalpically controlled, the retention factor and separation factor decreasing with increasing temperature, but entropically controlled separation was also observed. The elution sequences of the paroxetine enantiomers on the two pairs of pseudoenantiomeric CSPs were investigated, and an attempt was made to explain the observed anomalies in silico in order to gain an insight into the underlying molecular recognition events between the four chiral selectors and the analyte enantiomers.
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
CB - Analytical chemistry, separation
OECD FORD branch
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Result continuities
Project
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Continuities
N - Vyzkumna aktivita podporovana z neverejnych zdroju
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Pharmaceutical and Biomedical Analysis
ISSN
0731-7085
e-ISSN
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Volume of the periodical
124
Issue of the periodical within the volume
květen
Country of publishing house
GB - UNITED KINGDOM
Number of pages
10
Pages from-to
164-173
UT code for WoS article
000374202000019
EID of the result in the Scopus database
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