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Push or Pull for a Better Selectivity? A Study on the Electronic Effects of Substituents of the Pyridine Ring on the Enantiomeric Recognition of Chiral Pyridino-18-Crown-6 Ethers
- Source :
- Symmetry, Volume 12, Issue 11, Symmetry, Vol 12, Iss 1795, p 1795 (2020)
- Publication Year :
- 2020
- Publisher :
- Multidisciplinary Digital Publishing Institute, 2020.
-
Abstract
- Seven dimethyl-substituted optically active pyridino-18-crown-6 ethers containing various substituents at position 4 of the pyridine ring were studied with regards to the electron-donating and -withdrawing effects of substituents on enantiomeric recognition. In order to compile this set of compounds, we prepared four novel pyridino-18-crown-6 ethers, including an intermediate of a new synthetic route for a formerly reported crown ether. The discriminating ability of these pyridino-crown ethers with C2-symmetry toward the enantiomers of protonated primary amines was examined by isothermal titration calorimetry.
- Subjects :
- Physics and Astronomy (miscellaneous)
General Mathematics
complexation
010402 general chemistry
Ring (chemistry)
01 natural sciences
Medicinal chemistry
chemistry.chemical_compound
stomatognathic system
Pyridine
Computer Science (miscellaneous)
Electronic effect
Crown ether
chemistry.chemical_classification
010405 organic chemistry
lcsh:Mathematics
18-Crown-6
Isothermal titration calorimetry
enantiomeric recognition
lcsh:QA1-939
0104 chemical sciences
pyridine derivatives
chemistry
Chemistry (miscellaneous)
crown ether
Enantiomer
isothermal calorimetry
Selectivity
Subjects
Details
- Language :
- English
- ISSN :
- 20738994
- Database :
- OpenAIRE
- Journal :
- Symmetry
- Accession number :
- edsair.doi.dedup.....65793839b90afc1b65446bdba819118a
- Full Text :
- https://doi.org/10.3390/sym12111795