Theoretical Study on The Investigation of Antioxidant Properties of Some 4-Benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives

Yıl 2019, Cilt: 9 Sayı: 1, 512 - 521, 01.03.2019

Zeynep Turhan Irak , Murat Beytur

https://doi.org/10.21597/jist.481990

Cited By: 4

Öz

In this study, the antioxidant properties of
some experimentally determined
4-benzylideneamino-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives of
antioxidant properties were compared by density functional theory method.
Quantum chemical calculations based on density functional theory (DFT) were
employed to study the relationship between
4-benzylideneamino-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives (for 2a and
2g) having the highest and least antioxidant activity in experimental results. The solvation effects on
the antioxidant activity were taken into account by using the conductor-like
polarisable continuum model with different dielectric constants (ϵ= 2.25, C6H6;
ϵ = 78.39, H2O). The three antioxidant action mechanisms, hydrogen
atom transfer (HAT), single electron transfer-proton transfer (SET-PT) and
sequential protonloss electron transfer (SPLET) were elucidated. The reaction
enthalpies related to the steps in these mechanisms were computed in gas phase
and solvents, the compatibility of the calculated results with experimental
values ​​is discussed. The results showed that SPLET was the most favourable
mechanism for describing the antioxidant activity of 2a and 2g in the aqueous
phase, SPLET represented the most thermodynamically plausible reaction pathway. Calculations performed
by using DFT method at the rB3LYP/6-311++G (2d,2p) level of theory for neutral
molecules and anions in the gas and solvation phase, for radicals and cations,
uB3LYP/ 6-311++G (2d,2p) basis set has been used.

Anahtar Kelimeler

Antioxidant mechanism, radical scavenging activity, antioxidant descriptors, density theory, triazole

4-Benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on Türevlerinin Antioksidan Aktivitelerinin Teorik Olarak İncelenmesi

Öz

Bu çalışmada, antioksidan özellikleri deneysel
olarak belirlenmiş bazı 4-benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on
türevleri bileşiklerinin Yoğunluk Fonksiyonel Teorisi yöntemiyle antioksidan
etkinliklerinin karşılaştırılması yapılmıştır. Yoğunluk fonksiyonel teorisine
(DFT) dayanan kuantum kimyasal hesaplamalar, deneysel sonuçlarında en fazla ve
en az antioksidan aktiviteye sahip
4-benzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on türevlerinin (2a ve 2g
için) arasındaki ilişkiyi incelemek için kullanılmıştır. Antioksidan aktivitesi
üzerindeki solvasyon etkileri, farklı dielektrik sabitleri (ϵ = 2.25, C6H6;
ϵ = 78.39, H2O) ile iletken benzeri polarize süreklilik modeli
kullanılarak dikkate alınmıştır. Üç antioksidan reaksiyon mekanizması, hidrojen
atom transferi (HAT), tek elektron transfer-proton transferi (SET-PT) ve
ardışık proton kaybı elektron transferi (SPLET) açıklanmıştır. Bu
mekanizmalardaki adımlarla ilgili reaksiyon entalpileri gaz fazında ve
çözücülerde hesaplanmış, hesaplanan sonuçların deneysel değerlerle uyumluluğu
tartışılmıştır. Sonuçlar, SPLET'in sulu fazda 2a ve 2g’nin antioksidan
aktivitesini tanımlamak için en uygun mekanizma olduğunu göstermiştir, SPLET en
termodinamik olarak makul reaksiyon yolunu temsil etmiştir. Hesaplamalar, DFT
yöntemiyle nötral moleküller ve anyonlar için rB3LYP/ 6-311++G (2d,2p),
radikaller ve katyonlar için uB3LYP/ 6-311++G (2d,2p) temel setleri
kullanılarak yapılmıştır. 

Anahtar Kelimeler

Antioksidan mekanizma, radikal süpürme aktivitesi, antioksidan tanımlayıcılar, yoğunluk teorisi, triazol

Kaynakça

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