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

Yıl 2018, Cilt: 20 Sayı: 2, 109 - 123, 01.12.2018

Özlem Özdemir

https://doi.org/10.25092/baunfbed.412405

Cited By: 3

Öz

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 (K_a)
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. 

Anahtar Kelimeler

Schiff bazları, tautomerlik, kolorimetrik sensörler, serbest radikal süpürme aktivitesi

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

Öz

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.

Anahtar Kelimeler

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

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