Syntheses, spectroscopic and structural characterizations and metal ion binding properties of Schiff bases derived from 4′-aminobenzo-15-crown-5

Güler H., HAYVALI Z., Dal H., HÖKELEK T.

Polyhedron, vol.31, no.1, pp.688-696, 2012 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 31 Issue: 1
  • Publication Date: 2012
  • Doi Number: 10.1016/j.poly.2011.10.034
  • Journal Name: Polyhedron
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.688-696
  • Keywords: Crown ethers, Crystal structure, NMR spectroscopy, Potassium complexes, Sodium complexes, Solvent extraction
  • Ankara University Affiliated: Yes

Abstract

A series of benzyloxybenzaldehyde derivatives (1-4) were synthesized by the reactions of 4-(bromomethyl)benzonitrile with 4-hydroxy-3-methoxybenzaldehyde (vanillin), 2-hydroxy-3-methoxybenzaldehyde (o-vanillin), 2-hydroxy-4- methoxybenzaldehyde and 2-hydroxy-5-methoxybenzaldehyde. Condensation reactions among the new benzyloxybenzaldehyde derivatives (1-4) with 4′-aminobenzo- 15-crown-5 yielded the new Schiff base compounds (5-8). Sodium complexes (5a-8a) and potassium complexes (5b-8b) were prepared with NaClO4 and KI, respectively. All of these synthesized compounds were characterized on the basis of FT-IR, 1H and 13C NMR, mass spectrometry and elemental analyses data. The solid state structures of compounds 8 and 5a were determined by X-ray crystallography. The extraction abilities of compounds 5-8 were also evaluated in CH2Cl2 by using several main group and transition metal picrates, such as Na+, K+, Pb 2+, Cr3+, Ni2+, Cu2+ and Zn 2+. © 2011 Elsevier Ltd. All rights reserved.