Mono-cyclopentyl substituted 1,3,4]thiadiazole thione tautomer: study of the spectroscopic, geometric, thermal, and biological properties

Regarding the importance of thiol-thione tautomer structure and the existence of hydrogen bonding in thione tautomer structure and its effect on geometric, physicochemical, and biological properties, mono-cyclopentyl-substituted bismuthiol was synthesized via a telescopic process in a green medium....

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Main Authors: Basir, Nurul Fatimah Abdul, Ghafarikhaligh, Mahta, Johan, Mohd Rafie, Khaligh, Nader Ghaffari
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Published: Taylor & Francis Ltd 2024
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Online Access:http://eprints.um.edu.my/45791/
https://doi.org/10.1080/17415993.2024.2302032
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spelling my.um.eprints.457912024-11-12T04:25:38Z http://eprints.um.edu.my/45791/ Mono-cyclopentyl substituted 1,3,4]thiadiazole thione tautomer: study of the spectroscopic, geometric, thermal, and biological properties Basir, Nurul Fatimah Abdul Ghafarikhaligh, Mahta Johan, Mohd Rafie Khaligh, Nader Ghaffari QD Chemistry Regarding the importance of thiol-thione tautomer structure and the existence of hydrogen bonding in thione tautomer structure and its effect on geometric, physicochemical, and biological properties, mono-cyclopentyl-substituted bismuthiol was synthesized via a telescopic process in a green medium. The pure product was characterized by physical and spectroscopic techniques. The suitable crystals for single crystal study were obtained after trying different solvents and mixed solvents, and long clear needle-like crystals could be isolated from a mixture of n-hexane and ethyl acetate (volume ratio of 8:2). The FTIR spectra of bismuthiol, 2,5-bis-cyclopentylsulfanyl-1,3,4]thiadiazole, and 5-cyclopentylsulfanyl-3H-1,3,4]thiadiazole-2-thione were studied to define the characteristic wavenumbers of thiol and thione structures. A possible hyper-conjugative interaction between the S-H and pi bond of C=N, the existence of C=S and C-N-H. and stability of thione structure was demonstrated for the new product, which supports our prediction of thione or thiol structure using the study of IR spectra. Furthermore, the influence of change in 1,3,4-thiadiazol ring and the presence N-H functional group of thione structure on the transition phases and thermal stability of bismuthiol, bis-cyclopentyl-substituted, and mono-cyclopentyl-substituted bismuthiol were investigated using TGA/DTA and DSC profile analysis. The SwissADME tool was employed to predict the biocheminformatic information of bismuthiol, bis- and mono-cyclopentyl-substituted bismuthiols, which displayed high potential of all 1,3,4-thiadizole derivatives in pharmaceutical and medicine areas. Finally, an in vitro antibacterial activity of the mono- and bis-cyclopentyl substituted bismuthiol against the gram-negative (Escherichia coli ATCC 25922) and gram-positive (Staphylococcus aureus ATCC 25923) bacterial species was conducted by the disk diffusion method with cefazolin as a blank antibiotic. The results showed superior antibacterial efficiency of both derivatives. Taylor & Francis Ltd 2024-05 Article PeerReviewed Basir, Nurul Fatimah Abdul and Ghafarikhaligh, Mahta and Johan, Mohd Rafie and Khaligh, Nader Ghaffari (2024) Mono-cyclopentyl substituted 1,3,4]thiadiazole thione tautomer: study of the spectroscopic, geometric, thermal, and biological properties. Journal of Sulfur Chemistry, 45 (3). pp. 378-394. ISSN 1741-5993, DOI https://doi.org/10.1080/17415993.2024.2302032 <https://doi.org/10.1080/17415993.2024.2302032>. https://doi.org/10.1080/17415993.2024.2302032 10.1080/17415993.2024.2302032
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic QD Chemistry
spellingShingle QD Chemistry
Basir, Nurul Fatimah Abdul
Ghafarikhaligh, Mahta
Johan, Mohd Rafie
Khaligh, Nader Ghaffari
Mono-cyclopentyl substituted 1,3,4]thiadiazole thione tautomer: study of the spectroscopic, geometric, thermal, and biological properties
description Regarding the importance of thiol-thione tautomer structure and the existence of hydrogen bonding in thione tautomer structure and its effect on geometric, physicochemical, and biological properties, mono-cyclopentyl-substituted bismuthiol was synthesized via a telescopic process in a green medium. The pure product was characterized by physical and spectroscopic techniques. The suitable crystals for single crystal study were obtained after trying different solvents and mixed solvents, and long clear needle-like crystals could be isolated from a mixture of n-hexane and ethyl acetate (volume ratio of 8:2). The FTIR spectra of bismuthiol, 2,5-bis-cyclopentylsulfanyl-1,3,4]thiadiazole, and 5-cyclopentylsulfanyl-3H-1,3,4]thiadiazole-2-thione were studied to define the characteristic wavenumbers of thiol and thione structures. A possible hyper-conjugative interaction between the S-H and pi bond of C=N, the existence of C=S and C-N-H. and stability of thione structure was demonstrated for the new product, which supports our prediction of thione or thiol structure using the study of IR spectra. Furthermore, the influence of change in 1,3,4-thiadiazol ring and the presence N-H functional group of thione structure on the transition phases and thermal stability of bismuthiol, bis-cyclopentyl-substituted, and mono-cyclopentyl-substituted bismuthiol were investigated using TGA/DTA and DSC profile analysis. The SwissADME tool was employed to predict the biocheminformatic information of bismuthiol, bis- and mono-cyclopentyl-substituted bismuthiols, which displayed high potential of all 1,3,4-thiadizole derivatives in pharmaceutical and medicine areas. Finally, an in vitro antibacterial activity of the mono- and bis-cyclopentyl substituted bismuthiol against the gram-negative (Escherichia coli ATCC 25922) and gram-positive (Staphylococcus aureus ATCC 25923) bacterial species was conducted by the disk diffusion method with cefazolin as a blank antibiotic. The results showed superior antibacterial efficiency of both derivatives.
format Article
author Basir, Nurul Fatimah Abdul
Ghafarikhaligh, Mahta
Johan, Mohd Rafie
Khaligh, Nader Ghaffari
author_facet Basir, Nurul Fatimah Abdul
Ghafarikhaligh, Mahta
Johan, Mohd Rafie
Khaligh, Nader Ghaffari
author_sort Basir, Nurul Fatimah Abdul
title Mono-cyclopentyl substituted 1,3,4]thiadiazole thione tautomer: study of the spectroscopic, geometric, thermal, and biological properties
title_short Mono-cyclopentyl substituted 1,3,4]thiadiazole thione tautomer: study of the spectroscopic, geometric, thermal, and biological properties
title_full Mono-cyclopentyl substituted 1,3,4]thiadiazole thione tautomer: study of the spectroscopic, geometric, thermal, and biological properties
title_fullStr Mono-cyclopentyl substituted 1,3,4]thiadiazole thione tautomer: study of the spectroscopic, geometric, thermal, and biological properties
title_full_unstemmed Mono-cyclopentyl substituted 1,3,4]thiadiazole thione tautomer: study of the spectroscopic, geometric, thermal, and biological properties
title_sort mono-cyclopentyl substituted 1,3,4]thiadiazole thione tautomer: study of the spectroscopic, geometric, thermal, and biological properties
publisher Taylor & Francis Ltd
publishDate 2024
url http://eprints.um.edu.my/45791/
https://doi.org/10.1080/17415993.2024.2302032
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