New Schiff bases based on isatin and (thio)/carbohydrazone: preparation, experimental–theoretical spectroscopic characterization, and DFT approach to antioxidant characteristics

MUĞLU, Halit; Sönmez, Fatih; ÇAVUŞ, Muhammet Serdar; Kurt, Belma Z.; Yakan, Hasan

doi:10.1007/s11164-022-04908-1

New Schiff bases based on isatin and (thio)/carbohydrazone: preparation, experimental–theoretical spectroscopic characterization, and DFT approach to antioxidant characteristics

Yazarlar (5)

Prof. Dr. Halit MUĞLU Kastamonu Üniversitesi, Türkiye

Prof. Dr. Fatih Sönmez Sakarya University Of Applied Sciences, Türkiye

Prof. Dr. Muhammet Serdar ÇAVUŞ Kastamonu Üniversitesi, Türkiye

Belma Z. Kurt Bezmiâlem Vakıf Üniversitesi, Türkiye

Hasan Yakan Ondokuz Mayis Üniversitesi, Türkiye

Makale Türü	Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale)
Dergi Adı	Research on Chemical Intermediates (Q2)
Dergi ISSN	0922-6168 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler	SCI-Expanded
Makale Dili	İngilizce	Basım Tarihi	04-2023
Cilt / Sayı / Sayfa	49 / 4 / 1463–1484	DOI	10.1007/s11164-022-04908-1
Makale Linki	http://dx.doi.org/10.1007/s11164-022-04908-1

Özet

In this study, synthesis, spectroscopic elucidation, and investigation of antioxidant properties of new Schiff bases based on isatin and (thio)/carbohydrazone derivatives have been reported for the first time. The structures of the synthesized compounds were elucidated by FT-IR, ¹H-NMR, and ¹³C-NMR spectroscopic methods and elemental analysis. Their DPPH, ABTS, and CUPRAC activities were evaluated as antioxidant properties. Electronic and spectral data of the compounds were obtained by DFT calculations at the B3LYP/6–311+ +G(2d,2p) level of theory. Intramolecular interactions and charge densities on the bonds were analyzed by QTAIM and IRI calculations. In addition to parameters such as frontier molecular orbital energy eigenvalues, electronegativity, nucleophilicity index, and electrodonating power, the changes in the enthalpy of the compounds for the reactions realized through the SET mechanism were calculated to elucidate the antioxidant reactions of the compounds. Most of synthesized compounds exhibited antioxidant activities with the IC50 values ranging from 27.13 to 43.35 µM for DPPH, from 6.47 to 24.96 µM for ABTS and with the A0.50 values ranging from 9.04 to 47.52 µM for CUPRAC. Among them, compound 3, containing two hydroxyl groups, showed the strongest antioxidant activity for each assay (IC50 = 27.13 µM for DPPH, 6.47 µM for ABTS, and A0.50 = 9.04 µM for CUPRAC). The antioxidant activities of compound 3 were almost two or threefold weaker than that of BHA (IC50 = 9.55 µM for DPPH, 3.42 µM for ABTS, and A0.50 = 2.24 µM for CUPRAC), used as a standard. In addition, thiocarbohydrazone compounds exhibited higher antioxidant activity than carbohydrazones. Electron donating ability and single electron transfer enthalpy calculations predicted that thiocarbohydrazone compounds can perform SET reactions more easily than carbohydrazones.

Anahtar Kelimeler

Antioxidant assay | DFT | Isatin | Schiff bases | Spectroscopic elucidation

BM Sürdürülebilir Kalkınma Amaçları

Atıf Sayıları
Scopus	14

New Schiff bases based on isatin and (thio)/carbohydrazone: preparation, experimental–theoretical spectroscopic characterization, and DFT approach to antioxidant characteristics

Dergi Adı	RESEARCH ON CHEMICAL INTERMEDIATES
Yayıncı	Springer Netherlands
Açık Erişim	Hayır
ISSN	0922-6168
E-ISSN	1568-5675
CiteScore	5,7
SJR	0,528
SNIP	0,724

New Schiff bases based on isatin and (thio)/carbohydrazone: preparation, experimental–theoretical spectroscopic characterization, and DFT approach to antioxidant characteristics

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