Preparation, antioxidant activity, and theoretical studies on the relationship between antioxidant and electronic properties of bis(thio/carbohydrazone) derivatives

MUĞLU, Halit; Güzel, Emre; Yakan, Hasan; ÇAVUŞ, Muhammet Serdar; Sönmez, Fatih; Sönmez, Fatih; Kurt, Belma Zengin

doi:10.1016/j.jpcs.2022.110618

Preparation, antioxidant activity, and theoretical studies on the relationship between antioxidant and electronic properties of bis(thio/carbohydrazone) derivatives

Yazarlar (7)

Prof. Dr. Halit MUĞLU Kastamonu Üniversitesi, Türkiye

Prof. Dr. Emre Güzel Sakarya Uygulamalı Bilimler Üniversitesi, Türkiye

Doç. Dr. Hasan Yakan Ondokuz Mayıs Üniversitesi, Türkiye

Prof. Dr. Muhammet Serdar ÇAVUŞ Kastamonu Üniversitesi, Türkiye

Fatih Sönmez Sakarya University Of Applied Sciences, Türkiye

Prof. Dr. Fatih Sönmez Sakarya Uygulamalı Bilimler Üniversitesi, Türkiye

Prof. Dr. Belma Zengin Kurt Bezmiâlem Vakıf Üniversitesi, Türkiye

Makale Türü	Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale)
Dergi Adı	Journal of Physics and Chemistry of Solids (Q2)
Dergi ISSN	0022-3697 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler	SCI-Expanded
Makale Dili	Türkçe	Basım Tarihi	01-2022
Cilt / Sayı / Sayfa	164 / 1 / –	DOI	10.1016/j.jpcs.2022.110618
Makale Linki	http://dx.doi.org/10.1016/j.jpcs.2022.110618

Özet

A series of novel bis(thio/carbohydrazone) compounds has been prepared from (thio)/carbohydrazide and various aldehyde derivatives. FTIR, ¹H and ¹³C NMR spectroscopy, and elemental analysis have been used to elucidate the structures of synthesized compounds. Their antioxidant properties have been assessed using the DPPH, ABTS, and CUPRAC methods. Most of the synthesized compounds exhibited antioxidant activity in each assay. The effects of the electronic and structural properties of urea/thiourea groups on the antioxidant properties of the compounds have been investigated, and it was observed that thiourea-based compounds showed better antioxidant activity than structurally similar urea-based compounds. Among them, N′,N‴-1,4-phenylene-bis(methaneylylidene)-bis(N′-2-hydroxybenzylidene)methane-bis(thiohydrazide) (9) and N′,N‴-(1,4-phenylene-bis(methaneylylidene)-bis(N′-2,4-dihydroxybenzylidene)methane-bis(thiohydrazide) (11) showed higher ABTS activity (IC50 = 2.69 μM and 3.24 μM, respectively) than the reference butylated hydroxyanisole (BHA, IC50 = 3.42 μM). Moreover, compound 11 showed the strongest DPPH activity with an IC50 value of 5.77 μM, almost twofold higher than that of BHA (IC50 = 9.55 μM). Structural, spectral, and electronic analyses of the compounds have also been performed by DFT calculations at the B3LYP/6–311++g(2d,2p) level of theory. EDR, NCI, DOS, and QTAIM calculations have been carried out to analyze the bond properties of electronegative atoms and to investigate intramolecular interactions. DFT simulations have also been carried out in order to study the relationship between electronic characteristics and antioxidant activity.

Anahtar Kelimeler

Antioxidant activity | Carbohydrazones | DFT | Schiff base | Structure elucidation

Science Direct

BM Sürdürülebilir Kalkınma Amaçları

Atıf Sayıları
Scopus	24

Preparation, antioxidant activity, and theoretical studies on the relationship between antioxidant and electronic properties of bis(thio/carbohydrazone) derivatives

Dergi Adı	JOURNAL OF PHYSICS AND CHEMISTRY OF SOLIDS
Yayıncı	Elsevier Ltd
Açık Erişim	Hayır
ISSN	0022-3697
E-ISSN	1879-2553
CiteScore	9,2
SJR	0,816
SNIP	0,991

Preparation, antioxidant activity, and theoretical studies on the relationship between antioxidant and electronic properties of bis(thio/carbohydrazone) derivatives

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