C_2-Symmetric chiral diamine ligands for enantiomeric recognition of amino acid esters and mandelic acid by proton NMR titration method

Authors

HAYRİYE ARAL
TARIK ARAL
MEHMET ÇOLAK
BERRİN ZİYADANOĞULLARI
RECEP ZİYADANOĞULLARI

DOI

10.3906/kim-1207-58

Abstract

Two novel C_2-symmetric chiral diamines containing \alpha -phenylethyl and \alpha -(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 K_f up to 2481 M^{-1}) and good enantioselectivity (up to K_L/K_D = 4.08) towards the mandelic acid enantiomers. The results show that simple structured and easily accessible acyclic C_2-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, C_2 symmetric, chiral diamines, amino acids, mandelic acid, NMR titration

First Page

374

Last Page

382

Recommended Citation

ARAL, HAYRİYE; ARAL, TARIK; ÇOLAK, MEHMET; ZİYADANOĞULLARI, BERRİN; and ZİYADANOĞULLARI, RECEP (2013) "C_2-Symmetric chiral diamine ligands for enantiomeric recognition of amino acid esters and mandelic acid by proton NMR titration method," Turkish Journal of Chemistry: Vol. 37: No. 3, Article 6. https://doi.org/10.3906/kim-1207-58
Available at: https://journals.tubitak.gov.tr/chem/vol37/iss3/6