Synonyms:84877-69-0;O~2~,O~6~-Dimethyl pyridine-2,6-dicarbothioate;DTXSID80516290
The study focuses on the synthesis and characterization of eleven new chiral macrocycles (1-11) of the pyridino-18-crown-6 type. These compounds were prepared using various starting materials such as (S)-(+)-2-phenylglycine, formic acid, acetic anhydride, and diethylene glycol ditosylate, among others. The roles of these chemicals are crucial in the formation of the chiral diamines and glycols, which are then used to create the macrocyclic structures through cyclization reactions with compounds like dimethyl 2,6-pyridinedicarboxylate and O,O'-dimethyl 2,6-pyridinedicarbothioate. The study also investigates the enantiomeric recognition properties of these new chiral ligands with (R)- and (S)-[α-(1-naphthyl)ethyl]ammonium perchlorate using 'H NMR spectral techniques. The interactions and the degree of enantiomeric recognition are analyzed based on the differences in free energy of activation values (ΔG*) and log K values. Additionally, the X-ray analyses of the dithionoamido ligands (2, 6, and 8) reveal significant deviations of the S and N atoms from the plane of the pyridine ring, indicating structural distortions. The study provides insights into the factors influencing enantiomeric recognition and the potential applications of these chiral macrocycles in enantiomeric separations.
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