- Turkish Journal of Chemistry
- Vol: 37 Issue: 3
- C2-Symmetric chiral diamine ligands for enantiomeric recognition of amino acid esters and mandelic a...
C2-Symmetric chiral diamine ligands for enantiomeric recognition of amino acid esters and mandelic acid by proton NMR titration method
Authors : Hayriye Aral, Tarık Aral, Mehmet Çolak, Berrin Ziyadanoğullari, Recep Ziyadanoğullari
Pages : 374-382
Doi:10.3906/kim-1207-58
View : 14 | Download : 3
Publication Date : 9999-12-31
Article Type : Makaleler
Abstract :Two novel C2-symmetric chiral diamines containing a -phenylethyl and a -(1-naphthyl)ethyl chiral subunits were prepared with quantitative yields. Enantiomeric recognition properties of these simple structured diamine ligands towards D- and L-amino acid esters and D- and L-mandelic acid were examined by the 1H NMR titration method. These ligands exhibited strong complexation (with Kf up to 2481 M-1) and good enantioselectivity (up to KL/KD = 4.08) towards the mandelic acid enantiomers. The results show that simple structured and easily accessible acyclic C2-symmetrical compounds can also be used for enantiomeric recognition of racemic amino acids and mandelic acid in addition to complex molecules such as crown ethers and other cyclic molecules.Keywords : Enantiomeric recognition, C2 symmetric, chiral diamines, amino acids, mandelic acid, NMR titration