Enantioselective Recognition for Carboxylic Acids by Novel Chiral Macrocyclic Polyamides Derived from L-/D-tartaric Acid |
| |
Authors: | Baohua Li Xuemei Yang Xiaojun Wu Zengwei Luo Cheng Zhong |
| |
Institution: | College of Chemistry and Molecular Sciences, Wuhan University , Wuhan, 430072, PR China |
| |
Abstract: | The enantioselectivity of chiral macrocyclic polyamides 1–3 derived from L-/D-tartaric acid was investigated by using 1H NMR. All the macrocycles exhibited certain chiral recognition towards the enantiomers of the racemic carboxylic acids we had chosen. As a chiral solvating agent, the compound 3 has the excellent enantiomeric discriminating ability for mandelic acids and its derivatives, containing an α-OH at the chiral carbon, while the compound 2 has the best enantioselectivity towards dibenzoyltartaric acid. The molar ratio and the association constants of the compound 3 with each of the enantiomers of some guest molecules were determined by using the Job's plots and a nonlinear leastsquares fitting method, respectively. The effect of the structure of the hosts or guests on the enantioselectivity of the compound 1–3 has been explored. |
| |
Keywords: | Macrocyclic polyamides Chiral recognition Association constant Carboxylic acids |
|
|