Easily attainable new approach to mass yield ferrocenyl Schiff base and different metal complexes of ferrocenyl Schiff base through convenient ultrasonication-solvothermal method

  • Ahmed Mourtada Elseman*
  • , Ahmed Esmail Shalan
  • , Mohamed M. Rashad
  • , Ali M. Hassan
  • , Nabila M. Ibrahim
  • , Amr M. Nassar
  • *Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

A new alternative approach with crucial mass yield and high reaction rates is proposed for the synthesis of ferrocenyl Schiff bases using an ultrasonication-solvothermal method. Equimolar condensation of ferrocenecarboxaldehyde and 2-aminophenol interact with each other, giving 1-(1-[2-hydroxyphenyl-2-imino]methyl)-ferrocene (FcOH). Furthermore, this ligand forms 1:1 complexes with cobalt(II), nickel(II), copper(II), and palladium(II) ions. From the different spectral data, it is found that metal ions coordinate with ligands through the azomethine group and the deprotonated oxygen of the phenol groups. Moreover, FcOH and their complexes were characterized by elemental analysis, Fourier transform infrared, 1H nuclear magnetic resonance, and UV-visible spectrophotometry. The spectral data of FcOH and its metal complexes were discussed in connection with the structural changes due to complexation. Meanwhile, the information about geometric structures can be concluded from the electronic spectra and the magnetic moments. Plainly, electron spin resonance spectra of the Cu(II) complex revealed dx2−y2 as a ground state, suggesting a square planar geometry around the Cu(II) center. The direct optical band gap energy Eg values of cobalt, nickel, copper, and palladium complexes of FcOH are found to be 3.7, 3.9, 4.6, and 3.65 eV, respectively. 1-(1-[2-Hydroxyphenyl-2-imino]methyl)-ferrocene and its metal complexes were screened for antibacterial activity. The results depict that the metal complexes were found to be more strongly antibacterial than the guardian Schiff base ligand (FcOH) against one or more bacterial species. The minimum inhibitory concentrations of antimicrobial properties of the purified compound were determined using the broth microdilution method.

Original languageEnglish
Article numbere3639
JournalJournal of Physical Organic Chemistry
Volume30
Issue number6
DOIs
Publication statusPublished - 1 Jun 2017
Externally publishedYes

Keywords

  • ESR
  • Schiff bases
  • antimicrobial activity
  • ferrocenecarboxaldehyde
  • optical band gap
  • ultrasonication-solvothermal method

Fingerprint

Dive into the research topics of 'Easily attainable new approach to mass yield ferrocenyl Schiff base and different metal complexes of ferrocenyl Schiff base through convenient ultrasonication-solvothermal method'. Together they form a unique fingerprint.

Cite this