Synthesis and Evaluation of FICA Derivatives as Chiral Derivatizing Agents
| Autor: | Hiroyuki Teramae, Tomoyo Kamei, Tamiko Takahashi, Jyunichi Koyanagi |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Magnetic Resonance Spectroscopy
Proton Magnetic Resonance Spectroscopy Carboxylic Acids Substituent Fluorine-19 NMR 010402 general chemistry 01 natural sciences Medicinal chemistry chemistry.chemical_compound symbols.namesake Drug Discovery Alkane stereochemistry Chiral derivatizing agent Benzene Conformational isomerism Density Functional Theory 010405 organic chemistry Diastereomer Esters Stereoisomerism Fluorine General Chemistry General Medicine 0104 chemical sciences Gibbs free energy chemistry symbols |
| Zdroj: | Chemical and Pharmaceutical Bulletin. 68:818-821 |
| ISSN: | 1347-5223 0009-2363 |
| DOI: | 10.1248/cpb.c20-00307 |
| Popis: | 1-Fluoroindan-1-carboxyic acid (FICA) derivatives containing a monosubstituted benzene ring (1b-e) were synthesized as their methyl esters and their potential as chiral derivatizing agents (CDAs) were assessed by both 19F- and 1H-NMR spectroscopy. Introduction of a substituent at the 4-position in the benzene ring caused a 1.2-2 fold increase in ΔδF values when compared with that of FICA. This increase was investigated using a correlation model for 19F-NMR and by the order of the stability of the synperiplanar (sp) and antiperiplanar (ap) conformers of the (R,S) and (S,S) diastereomers from the Gibbs' free energy at 298.15 K. |
| Databáze: | OpenAIRE |
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