Synthesis, characterization, antimicrobial activity and DFT study of some novel Schiff bases
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2021
Authors
Salihović, Mirsada
Pazalja, Mirha
Špirtović Halilović, Selma
Veljović, Elma
Mahmutović-Dizdarević, Irma

Roca, Sunčica

Novaković, Irena

Trifunović, Snežana

Article (Published version)

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Two new Schiff bases derived from L-cysteine and substituted benzaldehyde were synthesized: the compound 1 [2-((2-chlorobenzylidene) amino)-3-mercaptopropanoic acid] and the compound 2 [3-mercapto-2-((2-methoxybenzylidene) amino) propanoic acid]. Their structures were confirmed by experimental FT-IR, NMR (1H, 13C), and theoretical methodology DFT (density functional theory). DFT calculations were based on global chemical reactivity indices calculated using the B3LYP/6–31G*, B3LYP/6–31G**, and B3LYP/6–31+G* theory levels. Experimentally and theoretically obtained values for FT-IR and NMR (1H, 13C) of test compounds showed good agreement. The reactivity descriptors of B3LYP (E, EHOMO, ELUMO, dipole moment, ∆ɛ, μ, η, ω) were calculated to predict the stability of newly synthesized compounds. The microbiological activity of the compounds was tested on several Gram-positive bacteria: Staphylococcus aureus, Bacillus subtilis, Clostridium sporogenes, Microccocus luteus and Microccocus flavus.... The following Gram-negative bacteria were used to test the compounds: Escherichia coli, Pseudomonas aeruginosa Proteus hauseri, Klebsiella pneumoniae, Salmonella enterica subsp. enterica serovar Enteritidis. Also, the activity on the following yeasts was examined: Candida albicans, Saccharomyces cerevisiae and fungal strain Aspergillus brasilliensis. The Schiff base with chlorine in the structure (the compound 1) has the best antimicrobial action against all tested microorganisms. The selected quantum chemical descriptors calculated for the compounds 1 and 2 have a close relationship with the antimicrobial activity.
Keywords:
Antimicrobial activity / DFT / Schiff bases / SynthesisSource:
Journal of Molecular Structure, 2021, 1241, 130670-Publisher:
- Elsevier
DOI: 10.1016/j.molstruc.2021.130670
ISSN: 0022-2860
WoS: 000670212600008
Scopus: 2-s2.0-85106877693
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IHTMTY - JOUR AU - Salihović, Mirsada AU - Pazalja, Mirha AU - Špirtović Halilović, Selma AU - Veljović, Elma AU - Mahmutović-Dizdarević, Irma AU - Roca, Sunčica AU - Novaković, Irena AU - Trifunović, Snežana PY - 2021 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4690 AB - Two new Schiff bases derived from L-cysteine and substituted benzaldehyde were synthesized: the compound 1 [2-((2-chlorobenzylidene) amino)-3-mercaptopropanoic acid] and the compound 2 [3-mercapto-2-((2-methoxybenzylidene) amino) propanoic acid]. Their structures were confirmed by experimental FT-IR, NMR (1H, 13C), and theoretical methodology DFT (density functional theory). DFT calculations were based on global chemical reactivity indices calculated using the B3LYP/6–31G*, B3LYP/6–31G**, and B3LYP/6–31+G* theory levels. Experimentally and theoretically obtained values for FT-IR and NMR (1H, 13C) of test compounds showed good agreement. The reactivity descriptors of B3LYP (E, EHOMO, ELUMO, dipole moment, ∆ɛ, μ, η, ω) were calculated to predict the stability of newly synthesized compounds. The microbiological activity of the compounds was tested on several Gram-positive bacteria: Staphylococcus aureus, Bacillus subtilis, Clostridium sporogenes, Microccocus luteus and Microccocus flavus. The following Gram-negative bacteria were used to test the compounds: Escherichia coli, Pseudomonas aeruginosa Proteus hauseri, Klebsiella pneumoniae, Salmonella enterica subsp. enterica serovar Enteritidis. Also, the activity on the following yeasts was examined: Candida albicans, Saccharomyces cerevisiae and fungal strain Aspergillus brasilliensis. The Schiff base with chlorine in the structure (the compound 1) has the best antimicrobial action against all tested microorganisms. The selected quantum chemical descriptors calculated for the compounds 1 and 2 have a close relationship with the antimicrobial activity. PB - Elsevier T2 - Journal of Molecular Structure T1 - Synthesis, characterization, antimicrobial activity and DFT study of some novel Schiff bases VL - 1241 SP - 130670 DO - 10.1016/j.molstruc.2021.130670 ER -
@article{ author = "Salihović, Mirsada and Pazalja, Mirha and Špirtović Halilović, Selma and Veljović, Elma and Mahmutović-Dizdarević, Irma and Roca, Sunčica and Novaković, Irena and Trifunović, Snežana", year = "2021", abstract = "Two new Schiff bases derived from L-cysteine and substituted benzaldehyde were synthesized: the compound 1 [2-((2-chlorobenzylidene) amino)-3-mercaptopropanoic acid] and the compound 2 [3-mercapto-2-((2-methoxybenzylidene) amino) propanoic acid]. Their structures were confirmed by experimental FT-IR, NMR (1H, 13C), and theoretical methodology DFT (density functional theory). DFT calculations were based on global chemical reactivity indices calculated using the B3LYP/6–31G*, B3LYP/6–31G**, and B3LYP/6–31+G* theory levels. Experimentally and theoretically obtained values for FT-IR and NMR (1H, 13C) of test compounds showed good agreement. The reactivity descriptors of B3LYP (E, EHOMO, ELUMO, dipole moment, ∆ɛ, μ, η, ω) were calculated to predict the stability of newly synthesized compounds. The microbiological activity of the compounds was tested on several Gram-positive bacteria: Staphylococcus aureus, Bacillus subtilis, Clostridium sporogenes, Microccocus luteus and Microccocus flavus. The following Gram-negative bacteria were used to test the compounds: Escherichia coli, Pseudomonas aeruginosa Proteus hauseri, Klebsiella pneumoniae, Salmonella enterica subsp. enterica serovar Enteritidis. Also, the activity on the following yeasts was examined: Candida albicans, Saccharomyces cerevisiae and fungal strain Aspergillus brasilliensis. The Schiff base with chlorine in the structure (the compound 1) has the best antimicrobial action against all tested microorganisms. The selected quantum chemical descriptors calculated for the compounds 1 and 2 have a close relationship with the antimicrobial activity.", publisher = "Elsevier", journal = "Journal of Molecular Structure", title = "Synthesis, characterization, antimicrobial activity and DFT study of some novel Schiff bases", volume = "1241", pages = "130670", doi = "10.1016/j.molstruc.2021.130670" }
Salihović, M., Pazalja, M., Špirtović Halilović, S., Veljović, E., Mahmutović-Dizdarević, I., Roca, S., Novaković, I.,& Trifunović, S.. (2021). Synthesis, characterization, antimicrobial activity and DFT study of some novel Schiff bases. in Journal of Molecular Structure Elsevier., 1241, 130670. https://doi.org/10.1016/j.molstruc.2021.130670
Salihović M, Pazalja M, Špirtović Halilović S, Veljović E, Mahmutović-Dizdarević I, Roca S, Novaković I, Trifunović S. Synthesis, characterization, antimicrobial activity and DFT study of some novel Schiff bases. in Journal of Molecular Structure. 2021;1241:130670. doi:10.1016/j.molstruc.2021.130670 .
Salihović, Mirsada, Pazalja, Mirha, Špirtović Halilović, Selma, Veljović, Elma, Mahmutović-Dizdarević, Irma, Roca, Sunčica, Novaković, Irena, Trifunović, Snežana, "Synthesis, characterization, antimicrobial activity and DFT study of some novel Schiff bases" in Journal of Molecular Structure, 1241 (2021):130670, https://doi.org/10.1016/j.molstruc.2021.130670 . .