Synthesis, Characterization and Antimicrobial Activity of Schiff Bases Including Three Hydroxy Groups and Their CoCl2, PdCl2, CuCl2 and ZnCl2 Complexes

Alterhoni E., Tavman A., Gürbüz D., HACIOĞLU M., Çinarli A., Şahin O., ...More

ChemistrySelect, vol.5, no.31, pp.9730-9735, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 5 Issue: 31
  • Publication Date: 2020
  • Doi Number: 10.1002/slct.202001498
  • Journal Name: ChemistrySelect
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Page Numbers: pp.9730-9735
  • Keywords: Antimicrobial, Chelates, Dihydroxy, 4-Methylphenol, Schiff bases, TRANSITION-METAL-COMPLEXES, TRANSFER RADICAL POLYMERIZATION, SPECTRAL CHARACTERIZATION, COPPER(II) COMPLEXES, THERMAL-PROPERTIES, CRYSTAL-STRUCTURE, NI(II) COMPLEXES, MANNICH-BASES, ANTIBACTERIAL, TETRADENTATE
  • Istanbul University Affiliated: Yes

Abstract

Four Schiff bases, (3/4/2/4)-{[(2-hydroxy-5-methylphenyl)imino]methyl}benzene-1,2/1,3/1,4/1,2-diols (H3L1-H3L4), derived from 2,3/2,4/2,5/3,4-dihydroxybenzaldehydes and 2-amino-4-methylphenol, and their CoCl2, PdCl2, CuCl(2)and ZnCl(2)complexes were synthesized and characterized. The structures of the complexes were suggested on the basis of elemental analysis, TGA, molar conductivity, magnetic moment, FT-IR, UV-vis and NMR spectroscopy. According to the analytical and spectral data, the ligandsH(3)L(1),H(3)L(2)andH(3)L(3)acted as tridentate, giving chelate structures in the complexes, via the C=N nitrogen and two phenolate oxygen atoms whereasH(3)L(4)acted as bidentate. In addition, the crystal structure ofH(3)L(1)was determined by X-ray diffraction. The spectral data show that there is keto-enol tautomerization in the ligands and keto form is dominant inH(3)L(1)andH(3)L(3)while enol form is inH(3)L(2)andH(3)L(4). Antimicrobial activities of the compounds were tested against six bacteria and three fungi. [Zn(H2L1)Cl].4H(2)O showed superior activity toward the fungiC. albicans,C. parapsilosisandC. tropicaliscompared toH(3)L(1)and the other compounds. Strong activity ofH(3)L(1),H(3)L(2)andH(3)L(3)was observed towardS. aureuswhereas they showed weak activity to the other microorganisms.