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Syntheses and spectroscopic characterization of double-armed benzo-15-crown-5 derivatives and their sodium and potassium complexes

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Abstract

A series of new benzo-15-crown-5 derivatives (1–6) containing formyl and imine groups were prepared. New formyl crown ethers (1 and 2) were prepared by reaction of 4′,5′-bis(bromomethyl)benzo-15-crown-5 with 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) and 2-hydroxy-5-methoxybenzaldehyde in the presence of NaOH. New Schiff bases (3–6) were synthesized by the condensation of corresponding aldehydes with 1,3-diaminopropane and 1,4-diaminobutane. Sodium and potassium complexes (1a–6a and 1b–6b) of the crown compounds forming crystalline complexes of 1:1 (Na+:ligand) and 1:2 (K+:ligand) stoichiometries were also synthesized. The structures of the aldehydes 1 and 2, imines 3–6 and complexes (1a–3a and 1b–3b) were confirmed on the basis of elemental analyses, IR, 1H- and 13C-NMR, and mass spectroscopy.

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Acknowledgments

The authors gratefully acknowledge the financial assistance of the Scientific and Technical Research Council of Turkey (TUBITAK), Grand No: TBAG 109T034.

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  1. Department of Chemistry, Faculty of Science, Ankara University, 06100, Ankara, Turkey

    Zeliha Hayvalı & Pınar Köksal

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  1. Zeliha Hayvalı
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  2. Pınar Köksal
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Correspondence to Zeliha Hayvalı.

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Hayvalı, Z., Köksal, P. Syntheses and spectroscopic characterization of double-armed benzo-15-crown-5 derivatives and their sodium and potassium complexes. J Incl Phenom Macrocycl Chem 76, 369–378 (2013). https://doi.org/10.1007/s10847-012-0208-7

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