Synthesis, spectral characterisation of 2-(5-methyl-1H-benzimidazol-2-yl)-4-bromo/nitro-phenols and their complexes with zinc(II) ion, and solvent effect on complexation.
2-(5-Methyl-1H-benzimidazol-2-yl)-4-bromo/nitro-phenols (HLBr and HLNO2) and their Zn(II) complexes with ZnX2 (X = Cl, I, NO3) were synthesized and characterized by elemental analysis, molar conductivity, IR, 1H and 13C NMR spectra. The OH proton appears near the NH protons in the 1H NMR spectra of the ligands because of the strong intramolecular hydrogen bonding between the OH hydrogen and the C=N nitrogen atoms. The complexation is investigated in ethanol and isopropanol and it is observed that isopropanol is a better solvent than ethanol for the complex forming. HLBr gives harder complexation reaction with Zn(II) according to HLNO2 because of the stronger intramolecular hydrogen bonding in HLBr, and the both ligands react easier with Zn(NO3)2 than ZnCl2 and ZnI2. The Zn(II) complexes of HLBr have 1:1 M:L ratio and ionic character, however, HLNO2 give a non-ionic complex that has 1:2 M:L ratio. In the complexes the phenolic hydrogen is eliminated and a chelate structure is formed.
Tavman
Aydin
A
Istanbul University, Faculty of Engineering, Department of Chemistry, 34320 Avcilar, Istanbul, Turkey. atavman@istanbul.edu.tr
D001562:Benzimidazoles / Q000737:chemistry*; D002247:Carbon Isotopes; D006860:Hydrogen Bonding; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D009596:Nitrophenols / Q000138:chemical synthesis* / Q000737:chemistry*; D011522:Protons; D012997:Solvents / Q000737:chemistry* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D015032:Zinc / Q000737:chemistry*
D001562:Benzimidazoles; D002247:Carbon Isotopes; D008024:Ligands; D009596:Nitrophenols; D011522:Protons; D012997:Solvents; D015032:Zinc