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

HAYVALI Z., Koksal P.

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, cilt.76, sa.3-4, ss.369-378, 2013 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 76 Sayı: 3-4
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1007/s10847-012-0208-7
  • Dergi Adı: JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.369-378
  • Anahtar Kelimeler: Crown compounds, Schiff bases, Aldehydes, Alkali metal complexes, Macrocycles, CROWN-ETHERS, LIQUID-EXTRACTION, RECOGNITION SITES, CYCLIC POLYETHERS, GUEST CATIONS, SCHIFF-BASES, METAL-IONS, PART I, ALKALI, COORDINATION
  • Ankara Üniversitesi Adresli: Evet

Özet

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, H-1- and C-13-NMR, and mass spectroscopy.