Synthesis of new bis(thiosemicarbazone) derivatives and DFT analysis of antioxidant characteristics in relation to HAT and SET reactions

MUĞLU H., ÇAVUŞ M. S., BAKIR T. K., Yakan H.

JOURNAL OF THE INDIAN CHEMICAL SOCIETY, cilt.99, sa.12, 2022 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 99 Sayı: 12
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1016/j.jics.2022.100789
  • Dergi Adı: JOURNAL OF THE INDIAN CHEMICAL SOCIETY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Analytical Abstracts, Chemical Abstracts Core, EMBASE, Index Chemicus (IC)
  • Anahtar Kelimeler: Thiosemicarbazone Schiff bases, Antioxidant activity, Spectroscopic studies, Quantum-chemical calculations, SCHIFF-BASES, THIOSEMICARBAZONE, ANTIBACTERIAL, SEMICARBAZONE, DOCKING, ANTICANCER, INHIBITORS, BEARING, DESIGN
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

A series of new bis(thiosemicarbazones) have been synthesized from terephthalaldehyde and various thiosemicarbazides. IR, H-1 NMR, C-13 NMR spectroscopic methods, and elemental analysis were used to characterize the identification of the synthesized compounds. The in vitro antioxidant activity determinations were made using the 1,1-Diphenyl-2-Picryl Hydrazil (DPPH) method. The compounds exhibited very different inhibition activities with the change of groups attached to the bis(thiosemicarbazone) structure. The spectral and electronic properties of the compounds were investigated by DFT calculation. Intramolecular interactions were analyzed by QTAIM and IRI calculations. Intrinsic bond strength index values of the N-H bonds, Fukui indices and the local electron affinities of the compounds were calculated, and the relationships between the compounds and their antioxidant activity properties were investigated. The SET and HAT mechanisms in the reactions of the compounds with DPPH were affected by the concentration of the compounds, and the possible effects of the parameters supporting the dominant characteristics in these reactions were examined using theoretical data.