Novel Bis-1,3,4-Thiadiazoles Derivatives: Synthesis, Spectroscopic Characterization, DFT Calculations and Evaluation of their Antimicrobial and Antioxidant Activities

Şükriye Çakmak; Muhammet Çavuş

doi:10.17776/csj.1221864

EN

Novel Bis-1,3,4-Thiadiazoles Derivatives: Synthesis, Spectroscopic Characterization, DFT Calculations and Evaluation of their Antimicrobial and Antioxidant Activities

Abstract

Two new, bis-1,3,4-thiadiazoles derivatives (I and II), were prepared by cyclization reaction of oxalic acid with N-alkyl/allyl thiosemicarbazides and phosphorous oxychloride (POCl3). Then the newly prepared products screened for their antimicrobial and antioxidant activities. The biological activity results shown that tested compounds exhibited effective antibacterial activity against six different bacteria. However, the compound II demonstrated greater ABTS˙+ scavenging ability. The characterization of the synthesized molecules was done by FT-IR, 1H NMR, 13C NMR spectroscopic methods and elemental analysis. Moreover, the experimental FT-IR and NMR spectra of the molecules were compared with the results calculated at the cc-pvtz, 6-311g(2d,2p), and 6-311++g(2d,2p) levels of theory. The effect of substituted groups on the spectral and electronic properties of the compounds was investigated. NCI and QTAIM analyses were performed to examine the effects of allyl group and intramolecular interactions on σ and π bonds. How the N-H bonds of the substituted groups affect the bond degrees was investigated using Fuzzy, Laplacian and Mayer approaches, and the relationship of the data with the antioxidant properties of the compounds was examined. In addition, the relationship between bond stretching force constant and intrinsic bond strength index, electron density, and delocalization index for some bonds was revealed.

Keywords

References

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Details

Primary Language

English

Subjects

-

Journal Section

Research Article

Authors

Şükriye Çakmak ^*
0000-0002-2221-0098
Türkiye

Muhammet Çavuş
0000-0002-3721-0883
Türkiye

Publication Date

March 26, 2023

Submission Date

December 20, 2022

Acceptance Date

March 1, 2023

Published in Issue

Year 2023 Volume: 44 Number: 1

DOI

https://doi.org/10.17776/csj.1221864

IZ

https://izlik.org/JA32MM49WZ

Cite

RIS / Bibtex

APA

Çakmak, Ş., & Çavuş, M. (2023). Novel Bis-1,3,4-Thiadiazoles Derivatives: Synthesis, Spectroscopic Characterization, DFT Calculations and Evaluation of their Antimicrobial and Antioxidant Activities. Cumhuriyet Science Journal, 44(1), 81-89. https://doi.org/10.17776/csj.1221864

Cited By

An Explicative Review of Thiadiazole: Medicinal Chemistry Aspects

Oriental Journal Of Chemistry

https://doi.org/10.13005/ojc/400632

Öz

Anahtar Kelimeler

Novel Bis-1,3,4-Thiadiazoles Derivatives: Synthesis, Spectroscopic Characterization, DFT Calculations and Evaluation of their Antimicrobial and Antioxidant Activities

Abstract

Keywords

References

Details

Primary Language

Subjects

Journal Section

Authors

Publication Date

Submission Date

Acceptance Date

Published in Issue

DOI

IZ

Cite

Cited By

An Explicative Review of Thiadiazole: Medicinal Chemistry Aspects