Enantiodiscrimination of Inherently Chiral Thiacalixarenes by Residual Dipolar Couplings
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F24%3A00568178" target="_blank" >RIV/61388963:_____/24:00568178 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22310/24:43927780 RIV/60461373:22810/24:43927780 RIV/00216208:11310/24:10467046 RIV/00216208:11320/24:10467046
Result on the web
<a href="https://doi.org/10.1021/acs.joc.2c02594" target="_blank" >https://doi.org/10.1021/acs.joc.2c02594</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.2c02594" target="_blank" >10.1021/acs.joc.2c02594</a>
Alternative languages
Result language
angličtina
Original language name
Enantiodiscrimination of Inherently Chiral Thiacalixarenes by Residual Dipolar Couplings
Original language description
Inherently chiral compounds, such as calixarenes, are chiral due to a nonplanar three-dimensional (3D) structure. Determining their conformation is essential to understand their properties, with nuclear magnetic resonance (NMR) spectroscopy being one applicable method. Using alignment media to measure residual dipolar couplings (RDCs) to obtain structural information is advantageous when classical NMR parameters like the nuclear Overhauser effect (NOE) or J-couplings fail. Besides providing more accurate structural information, the alignment media can induce different orientations of enantiomers. In this study, we examined the ability of polyglutamates with different side-chain moieties─poly-γ-benzyl-l-glutamate (PBLG) and poly-γ-p-biphenylmethyl-l-glutamate (PBPMLG) ─to enantiodifferentiate the inherently chiral phenoxathiin-based thiacalix[4]arenes. Both media, in combination with two solvents, allowed for enantiodiscrimination, which was, to the best of our knowledge, proved for the first time on inherently chiral compounds. Moreover, using the experimental RDCs, we investigated the calix[4]arenes conformational preferences in solution, quantitatively analyzed the differences in the alignment of the enantiomers, and discussed the pitfalls of the use of the RDC analysis.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GA20-08667S" target="_blank" >GA20-08667S: Chemistry of phenoxathiin-based thicalixarenes and related compounds</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2024
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 Organic Chemistry
ISSN
0022-3263
e-ISSN
1520-6904
Volume of the periodical
89
Issue of the periodical within the volume
14
Country of publishing house
US - UNITED STATES
Number of pages
10
Pages from-to
9711-9720
UT code for WoS article
000920494700001
EID of the result in the Scopus database
2-s2.0-85146570802