Polar and nonpolar iron (II) complexes of isatin hydrazone derivatives as effective catalysts in oxidation reactions and their antimicrobial and anticancer activities
Nehal Mamdouh A. El‐Sayed, Hany Elsawy, Mohamed Shaker S. Adam
Abstract
Two iron (II) complexes of various derivatives (polar with 5‐sodium sulfoante group and nonpolar with di‐ tert butyl groups, HLSO 3 Na and HLDBu, respectively) of isatin hydrazones were synthesized within 1:2 molar ratios of Fe 2+ ion to the isatin hydrazone ligand giving Fe (LSO 3 Na) 2 and Fe (LDBu) 2 , respectively. The polar and nonpolar isatin hydrazone derivatives behaved as O , N , O ‐tridentate pincer chelating agents with Fe 2+ ions. The variation in polarity of the two Fe 2+ ‐complexes controlled their catalytic action in the oxidation of alcohols using t BuOOH ( tert ‐butyl hydroperoxide). The polar catalyst showed more enhanced catalytic behavior than that of the nonpolar one. The optimized conditions for Fe (LDBu) 2 was found to be better at 70°C after 4 h with 86% of benzaldehyde than that with Fe (LSO 3 Na) 2 (at 90°C after 2 h with 84% of benzaldehyde). Their kinetic studies were used to derive the thermodynamic parameters of E a and ΔG # for the catalytic processes. Biologically, based on their high reactivity toward some bacterial and fungal strains and some human cancer cell lines, the calf thymus‐DNA ( ct DNA) interaction of the current compounds were studied. The nonpolar Fe 2+ ‐complex (Fe (LDBu) 2 ) assigned more reactivity with ct DNA more than that of the polar reagent (Fe (LSO 3 Na) 2 ) and also more than that of their uncoordinated ligands depending on their lipophilicity. Their reactivities toward ct DNA was established spectrophotometrically and within the changes in the DNA solution viscosity. The binding strength was evaluated with the magnitudes of the binding constant ( K b = 3.03, 3.21, 9.79, and 11.51 × 10 8 mol −1 dm 3 for HLDBu, HLSO 3 Na, Fe (LDBu) 2 , and Fe (LSO 3 Na) 2 , respectively), which supported by the Gibbs' free energy values −3.12, −31.42, −34.18, and −34.58 kJ mol −1 , respectively.