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Relevant academic research and scientific papers

Enantioselective complexation of chiral lariat crown ethers and chiral primary alkylammonium perchlorates

In order to investigate the enantiomeric recognition abilities toward 2 chiral alkylammonium perchlorates (AmI, AmII) by 1 H-NMR titration method in CDCl3, 4 chiral lariat ethers 8-11 with a (p-methoxyphenoxy) methyl flexible side arm were used. The most effective enantiomeric recognition was obtained by LCEs 9 and 11 toward AmII, by K R/KS 6.58 and KS/KR 6.63, respectively. The effect of macroring size, subunit of macroring, and side arm appeared to have strong influence on the binding ability of these alkylammonium ions. TUeBITAK.

Crystallographic evidence of side-arm lariat effect in the series of chiral ortho- and para-methoxyphenoxymethyl-15-crown-5 complexes with sodium perchlorate

The single crystals of the NaClO4 complexes with two potential lariat 15-crowns-5 having ortho- or para-methoxyphenoxymethyl side arms were investigated by X-ray analysis in racemic and enantiopure form. Only ortho-derivative demonstrates laria

Synthesis and extraction properties of some lariat ethers derived from the spontaneously resolved guaifenesin, 3-(2-methoxyphenoxy)propane-1,2-diol

Capable of spontaneous resolution rac-3-(2-methoxyphenoxy)propane-1,2-diol, guaifenesin 1 has been proposed as a cheap and readily available enantiopure precursor for the synthesis of nonracemic crown ethers having ligating OAr and OMe arms (lariat ethers). The crowns studied failed to form stable host/guest complexes with amine hydrochloride salts; the effective complexation was achieved using hexafluorophosphate salts. Moderate enantiomeric recognition of R*NH2·HPF6 was achieved with the lariat ethers 11c. As a whole, the enantioselectivity of the extraction is inversely related to the extractive power of the lariat ether. ARKAT-USA, Inc.

Chiral lariat ethers as membrane carriers for chiral amino acids and their sodium and potassium salts

Four chiral lariat ethers 8-11 containing a (p-methoxyphenoxy) methyl side arm were used for chiral discrimination of amino acids in their zwitterionic form or as potassium and sodium salts in transport across a bulk chloroform membrane with satisfactory selectivity. The carriers that were employed exhibited different transport selectivity relative to the amino acids and their salts under study. The d/l selectivity strongly depends on the amino acids or their salts, and in some cases reverse selectivity has been obtained. The best selectivity was obtained in the case of tyrosine and its potassium salts for all carriers. The transport rates of amino acids and their salts were found to be controlled by factors such as the structure of the carriers and amino acids or their salts. Among these factors, it was also found that the side arm of the lariat ethers plays an important role in the transport process. As a consequence, the main goal of our investigation was to separate the chiral amino acids through liquid membranes.

Synthesis and crystal structure of chiral substituted (S)-2-[(4- methoxyphenoxy) methyl]-15-crown-5 ether with sodium perchlorate complex

The crystal and molecular structure of chiral crown ether, (S)-2-[(4-methoxyphenoxy)methyl]-15-crown-5...NaClO4, has been determined by single-crystal X-ray diffraction. The complex crystallizes in the orthorombic space group Pbca with Z = 8. Lattice parameters are a = 11.451(2), b = 12.842(3), c = 31.330(7) A. The structure was refined to R factor of 0.0547. The Na ion is heptacoordinated. The Na-Oether distances range from 2.363(4) to 2.433(4) A and average 2.404(5) A. Perchlorate anion is bounded to sodium ion asymmetrically; the Na-O8 and Na-O9 distances are 2.444(5) A and 2.607(5) A. The C-O and C-C distances of the 15-membered ring average 1.419(9) and 1.478(12) A while the O-C-C and C-O-C angles average 108.2(6°) and 115.4(6°).

Synthesis of new chiral crown ethers containing a (p-methoxyphenoxy)methyl moiety and their chiral recognition ability towards amino acid esters

Novel crown ethers 9-13 containing a chiral subunit derived from 3-(p-methoxyphenoxy)propane-1,2-diol 7 were prepared in enantiomerically pure forms. Chiral recognition properties of these receptors towards L- and D-amino acid derivatives were examined by the UV-vis titration method. These receptors exhibit good chiral recognition towards the isomers (up to KL/K D = 5.81, ΔΔG0 = 4.30 kJ mol-1) in CHCl3 at 25°C.