Yeni sentezlenmiş naftaldimin-temelli tetraimin Schiff bazında fenol-keto tautomerliğinin, metal iyon bağlama ve serbest radikal süpürme özelliklerinin çalışılması

Bu çalışmada, sırasıyla D1 diimin Schiff bazının sentezlenmesi, bu Schiff bazının nitro grubunun amino grubuna indirgenmesi ve amino grubunun 2-hidroksi-1-naftaldehit ile etkileştirilmesi ile yeni dört imin grubu bulunan Schiff bazı (T1) sentezlendi. Bileşik çeşitli spektroskopik teknikler ile karakterize edildi. Schiff bazındaki (T1) fenol-keto tautomerliği farklı çözücü ve ortamlarda UV-GB spektrumları ile incelendi. T1 ile bazı metal iyonları Cr3+, Fe3+, Ni2+, Zn2+, Cu2+, Co2+, Pb2+, Ag+ and Ba2+ arasındaki bağlanma etkileşimi DMF-HEPES tampon karışımında (v/v, 1:1) UV–GB spektrofotometrisi ile belirlendi. Sonuçlar tercih edilen bağlanmanın Cu2+, Co2+ ve Fe3+ iyonları ile olduğunu gösterdi. Cu2+, Co2+ and Fe3+ iyonu varlığında, T1 çözeltisinin rengi sarıdan renksiz olacak şekilde değişti. T1 ile Cu2+, Co2+ ve Fe3+ iyonları arasında 1:1 bağlanma olduğu Job’s eğrisi yönteminden belirlendi. Bağlanma sabitleri (Ka) Cu2+, Co2+ ve Fe3+ iyonları için sırasıyla Benesi–Hildebrand eşitliğinden 1.22 x 104 M-1, 1.62 x 104 M-1 ve 5.79 x 104 M-1 olarak hesaplandı. Ayrıca, T1’in DPPH radikallerine karşı potansiyel bir süpürücü olduğu, yüzde 50 süpürme konsantrasyon değerinin standard askorbik asitten çok az büyük olduğu belirlendi.

Studies on phenol-keto tautomerism, metal ion binding, and free radical scavenging properties of newly synthesized naphthalene-based tetraimine Schiff base

In this study, a new tetraimine Schiff base (T1) was obtained by the synthesis of diimine Schiff base (D1), the reduction of nitro group of this Schiff base to amino group and the reacting of amino group with 2-hydroxy-1-naphthaldehyde, respectively. It was characterized by various spectroscopic techniques. The phenol-keto tautomerism of Schiff base (T1) was investigated by UV–vis spectra in different solvents and media. The binding interaction between T1 and metal ions, i.e., Cr3+, Fe3+, Ni2+, Zn2+, Cu2+, Co2+, Pb2+, Ag+ and Ba2+ was confirmed in DMF-HEPES buffer (v/v, 1:1) by UV–vis spectroscopy. It showed the favorable coordination toward Cu2+, Co2+ and Fe3+ ions. In the presence of Cu2+, Co2+ and Fe3+ ions, yellow color of T1 solution changed to colorless. The 1:1 binding stoichiometry between T1 and Cu2+, Co2+, Fe3+ ions was established using Job’s plot. The binding constants (Ka) were calculated to be 1.22 x 104 M-1, 1.62 x 104 M-1 and 5.79 x 104 M-1 for Cu2+, Co2+ and Fe3+ ions, respectively, by Benesi–Hildebrand equation. In addition, T1 was also found to be potent scavenger of DPPH radicals with half-maximal scavenging concentration (SC50) value less high than that of the standard, ascorbic acid.

Keywords:

Schiff bases, tautomerism, colorimetric sensors free radical scavenging activity,

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