The synthesis, Na+ binding properties of new coumarin-crown ethers

• Published in: Journal of inclusion phenomena and macrocyclic chemistry Vol. 78; no. 1-4; pp. 179 - 184
• Main Authors: Basaran, Ismet, Cakir, Umit
• Format: Journal Article
• Language: English
• Published: Dordrecht Springer Netherlands 01-04-2014
• Subjects: Chemistry; Chemistry and Materials Science; Crystallography and Scattering Methods; Food Science; Organic Chemistry; Original Article; Complexation; Synthesis; Coumarin-crown ethers; Conductometry
• ISSN: 1388-3127; 1573-1111
• DOI: 10.1007/s10847-013-0286-1

o
-Dihydroxy-3-(methylphenyl)-chromenones (coumarins;
3a
–
3c
) were synthesized from trimethoxybenzaldehydes through a reaction with the corresponding methylphenyl-acrylonitrile in pyridine·HCl and then H
3
O
+
. Dihydroxycoumarins reacted with the ditosylate or dichloride derivatives of tri- or tetraethyleneglycols in the presence of CH
3
CN/Na
2
CO
3
and macrocyclic ethers with a coumarin moiety were obtained. The chromatographically purified new coumarin-crown ethers (
5a–5f
) were identified by IR,
1
H NMR, and Mass spectrometry. The binding constants of Na
+
with the coumarin-crown ethers were determined in an 80 % dioxane/water binary solvent system at 25 °C from conductance measurements.