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Synthesis and spectroscopic characterization of asymmetric Schiff bases derived from 4′-formylbenzo-15-crown-5 containing recognition sites for alkali and transition metal guest cations

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Abstract

Asymmetric salen-type Schiff base ligands have been synthesized via a stepwise approach. In the first step, mono-Schiff base compounds were prepared by condensation of salicylaldehyde, 2-hydroxy-3-methoxybenzaldehyde, 2-hydroxy-5-methoxybenzaldehyde and 2-hydroxy-1-naphthaldehyde with hydrazine hydrate. These compounds were then reacted with 4′-formylbenzo-15-crown-5 to prepare asymmetric ligands. 1H-NMR spectra indicate that the mono- and asymmetric bis-Schiff base compounds exist in both (E) and (Z) isomeric forms in CDCl3 solution. The asymmetric crown compounds form crystalline 1:1 (Na+:ligand) complexes with sodium perchlorate. Homo-metallic Ni(II) and Zn(II) complexes with 1:2 (metal:ligand) stoichiometries have also been synthesized. The results indicate that the Schiff base ligands coordinate through the azomethine nitrogen and phenolic oxygen.

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Acknowledgements

The authors gratefully acknowledge the financial support of the Scientific and Technical Research Council of Turkey (TUBITAK), Grant number TBAG 107T002 and Ankara University Research Fund, Grant number 20020705070.

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Authors and Affiliations

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

    Zeliha Hayvali & Didem Yardimci

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  1. Zeliha Hayvali
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  2. Didem Yardimci
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Correspondence to Zeliha Hayvali.

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Hayvali, Z., Yardimci, D. Synthesis and spectroscopic characterization of asymmetric Schiff bases derived from 4′-formylbenzo-15-crown-5 containing recognition sites for alkali and transition metal guest cations. Transition Met Chem 33, 421–429 (2008). https://doi.org/10.1007/s11243-008-9060-4

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  • DOI: https://doi.org/10.1007/s11243-008-9060-4

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