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- Title
Enantiomeric discrimination of chiral organic salts by chiral aza-15-crown-5 ether with C <sub>1</sub> symmetry: experimental and theoretical approaches.
- Authors
Kocakaya, Safak Özhan; Turgut, Yılmaz; Pirinççioglu, Necmettin
- Abstract
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 (88–1,389 M−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 0.80 kcal mol−1, respectively. The differences in theoretical binding energies were calculated by MM-PBSA (ΔE RPB − ΔE SPB=) 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 1.66 kcal 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.
- Publication
Journal of Molecular Modeling, 2015, Vol 21, Issue 3, p1
- ISSN
1610-2940
- Publication type
Article
- DOI
10.1007/s00894-015-2604-6