Chiral calix[4]azacrowns for enantiomeric recognition of amino acid derivatives |
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Authors: | Havva Nur Demirtas |
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Institution: | Department of Chemistry, Selçuk University, 42099 Konya, Turkey |
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Abstract: | In this study the synthesis of novel chiral calix4]azacrown derivatives has been reported. The enantioselectivity of chiral receptors was investigated by using UV-vis spectroscopy. All the chiral calix4]arene derivatives exhibited certain chiral recognition toward the enantiomers of phenylalanine (Phe-OMe·HCl) and alanine methyl ester hydrochlorides (Ala-OMe·HCl). As a chiral receptor, the furfuryl-armed calix4]azacrown ether 7 has the best enantiomeric discriminating ability for α-amino acid ester hydrochlorides (up to KL/KD=2.08, ΔΔG0=−1.82 kJ mol−1) in CHCl3. The enantiomeric recognition abilities for guests are also discussed from a thermodynamic point of view. |
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