Limitations of Trifluoromethylbenzoimidazolylbenzoic Acid as a Chiral Derivatizing Agent to Assign Absolute Configuration for β-Chiral Aminoalcohols
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F22%3A73615683" target="_blank" >RIV/61989592:15310/22:73615683 - isvavai.cz</a>
Result on the web
<a href="https://pubs.acs.org/doi/pdf/10.1021/acsomega.1c07234" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acsomega.1c07234</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acsomega.1c07234" target="_blank" >10.1021/acsomega.1c07234</a>
Alternative languages
Result language
angličtina
Original language name
Limitations of Trifluoromethylbenzoimidazolylbenzoic Acid as a Chiral Derivatizing Agent to Assign Absolute Configuration for β-Chiral Aminoalcohols
Original language description
Axially chiral 2-(2-(trifluoromethyl)-1H-benzo[d]imidazole-1-yl)benzoic acid (TBBA) was used as a chiral derivatizing agent to evaluate the limits of absolute configuration assignment for β-chiral aminoalcohols. Seven Boc-aminoalcohols and eight variously N-substituted (S)-phenylglycinols were prepared, and their TBBA esters were analyzed by NMR spectroscopy. Diverse substitution at the β-position was employed to demonstrate the effect of structure on the general conformational model and reliability of the absolute configuration assignment. It was concluded that hydrogen bond formation and steric hindrance were the main factors affecting the correct assignment for Boc-aminoalcohols.
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
—
Continuities
S - Specificky vyzkum na vysokych skolach
Others
Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ACS Omega
ISSN
2470-1343
e-ISSN
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Volume of the periodical
7
Issue of the periodical within the volume
15
Country of publishing house
US - UNITED STATES
Number of pages
13
Pages from-to
"12734–12746"
UT code for WoS article
000812552700001
EID of the result in the Scopus database
2-s2.0-85128259427