Enantiomeric discrimination of chiral organic salts by chiral aza-15-crown-5 ether with C 1 symmetry: experimental and theoretical approaches
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| 024 | 7 | 0 | |a 10.1007/s00894-015-2604-6 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00894-015-2604-6 | ||
| 245 | 0 | 0 | |a Enantiomeric discrimination of chiral organic salts by chiral aza-15-crown-5 ether with C 1 symmetry: experimental and theoretical approaches |h [Elektronische Daten] |c [Safak Kocakaya, Yılmaz Turgut, Necmettin Pirinççioglu] |
| 520 | 3 | |a The work involves an experimental (1H NMR) and theoretical (MD, MM-PBSA and DFT) investigation of the molecular recognition and discrimination properties of a chiral aza-15-crown-5 against methyl esters of alanine, phenylalanine and valine hydrochloride salts. The results indicate that the receptor binds enantiomers with moderate binding constants (88-1,389M−1), with phenylalanine being more discriminated. The difference in experimental binding free energies (ΔG R−ΔG S) for alanine, phenylalanine and valine enantiomers were calculated as −0.36, −1.58 and 0.80kcal mol−1, respectively. The differences in theoretical binding energies were calculated by MM-PBSA (ΔE R PB−ΔE S PB=) as −0.30, −1.45 and 0.88, by B3LYP/6-31+G(d) as −1.17, −0.84 and 0.74 and by M06-2X/6-31+G(d) as −1.40, −3.26 and 1.66kcal mol−1. The data obtained give valuable information regarding the molecular recognition mode of the organoammonium complexes of chiral aza-crown ether with C 1 symmetry, which may be relevant to biological systems. Graphical Abstract Left Superimposed lowest energy conformers of complexes of chiral aza-crown ether with theenantiomersof phenylalanineobtained from cluster analysis of MD trajectories. Right Non-linear dependence of 1H NMR chemical shifts of methyl groups of isopropyl in receptor 5 on the concentration of the enantiomers of valine ester salts | |
| 540 | |a Springer-Verlag Berlin Heidelberg, 2015 | ||
| 690 | 7 | |a Enantiomeric discrimination |2 nationallicence | |
| 690 | 7 | |a Chiral aza-crown ether |2 nationallicence | |
| 690 | 7 | |a Molecular recognition |2 nationallicence | |
| 690 | 7 | |a Amino acid ester salt |2 nationallicence | |
| 690 | 7 | |a 1H NMR titration |2 nationallicence | |
| 690 | 7 | |a Computational calculation |2 nationallicence | |
| 690 | 7 | |a Molecular dynamics |2 nationallicence | |
| 690 | 7 | |a MM-PBSA |2 nationallicence | |
| 690 | 7 | |a DFT |2 nationallicence | |
| 700 | 1 | |a Kocakaya |D Safak |u Department of Chemistry, Faculty of Science, University of Dicle, 21280, Diyarbakir, Turkey |4 aut | |
| 700 | 1 | |a Turgut |D Yılmaz |u Department of Chemistry, Faculty of Science, University of Dicle, 21280, Diyarbakir, Turkey |4 aut | |
| 700 | 1 | |a Pirinççioglu |D Necmettin |u Department of Chemistry, Faculty of Science, University of Dicle, 21280, Diyarbakir, Turkey |4 aut | |
| 773 | 0 | |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/3(2015-03-01), 1-13 |x 1610-2940 |q 21:3<1 |1 2015 |2 21 |o 894 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00894-015-2604-6 |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00894-015-2604-6 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Kocakaya |D Safak |u Department of Chemistry, Faculty of Science, University of Dicle, 21280, Diyarbakir, Turkey |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Turgut |D Yılmaz |u Department of Chemistry, Faculty of Science, University of Dicle, 21280, Diyarbakir, Turkey |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Pirinççioglu |D Necmettin |u Department of Chemistry, Faculty of Science, University of Dicle, 21280, Diyarbakir, Turkey |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/3(2015-03-01), 1-13 |x 1610-2940 |q 21:3<1 |1 2015 |2 21 |o 894 | ||