Ajdačić, Vladimir

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orcid::0000-0002-3423-0862
  • Ajdačić, Vladimir (8)

Author's Bibliography

Direct glyphosate soil monitoring at the triazine-based covalent organic framework with the theoretical study of sensing principle

Knežević, Sara; Terzić-Jovanović, Nataša; Vlahović, Filip; Ajdačić, Vladimir; Costache, Vlad; Vidić, Jasmina; Opsenica, Igor; Stanković, Dalibor

(Elsevier, 2023)

TY  - JOUR
AU  - Knežević, Sara
AU  - Terzić-Jovanović, Nataša
AU  - Vlahović, Filip
AU  - Ajdačić, Vladimir
AU  - Costache, Vlad
AU  - Vidić, Jasmina
AU  - Opsenica, Igor
AU  - Stanković, Dalibor
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7175
AB  - Covalent organic frameworks (COFs) are emerging as promising sensing materials due to their controllable structure and function properties, as well as excellent physicochemical characteristics. Here, specific interactions between a triazine-based COF and a mass-used herbicide – glyphosate (GLY) have been utilized to design a disposable sensing platform for GLY detection. This herbicide has been extensively used for decades, however, its harmful environmental impact and toxicity to humans have been recently proven, conditioning the necessity for the strict control and monitoring of its use and its presence in soil, water, and food. Glyphosate is an organophosphorus compound, and its detection in complex matrices usually requires laborious pretreatment. Here, we developed a direct, miniaturized, robust, and green approach for disposable electrochemical sensing of glyphosate, utilizing COF's ability to selectively capture and concentrate negatively charged glyphosate molecules inside its nanopores. This process generates the concentration gradient of GLY, accelerating its diffusion towards the electrode surface. Simultaneously, specific COF-glyphosate binding catalyses the oxidative cleavage of the C–P bond and, together with pore nanoconfinement, enables sensitive glyphosate detection. Detailed sensing principles and selectiveness were scrutinized using DFT-based modelling. The proposed electrochemical method has a linear working range from 0.1 μM to 10 μM, a low limit of detection of 96 nM, and a limit of quantification of 320 nM. The elaborated sensing approach is viable for use in real sample matrices and tested for GLY determination in soil and water samples, without pretreatment, preparation, or purification. The results showed the practical usefulness of the sensor in the real sample analysis and suggested its suitability for possible out-of-laboratory sensing.
PB  - Elsevier
T2  - Chemosphere
T1  - Direct glyphosate soil monitoring at the triazine-based covalent organic framework with the theoretical study of sensing principle
VL  - 341
SP  - 139930
DO  - 10.1016/j.chemosphere.2023.139930
ER  - 
@article{
author = "Knežević, Sara and Terzić-Jovanović, Nataša and Vlahović, Filip and Ajdačić, Vladimir and Costache, Vlad and Vidić, Jasmina and Opsenica, Igor and Stanković, Dalibor",
year = "2023",
abstract = "Covalent organic frameworks (COFs) are emerging as promising sensing materials due to their controllable structure and function properties, as well as excellent physicochemical characteristics. Here, specific interactions between a triazine-based COF and a mass-used herbicide – glyphosate (GLY) have been utilized to design a disposable sensing platform for GLY detection. This herbicide has been extensively used for decades, however, its harmful environmental impact and toxicity to humans have been recently proven, conditioning the necessity for the strict control and monitoring of its use and its presence in soil, water, and food. Glyphosate is an organophosphorus compound, and its detection in complex matrices usually requires laborious pretreatment. Here, we developed a direct, miniaturized, robust, and green approach for disposable electrochemical sensing of glyphosate, utilizing COF's ability to selectively capture and concentrate negatively charged glyphosate molecules inside its nanopores. This process generates the concentration gradient of GLY, accelerating its diffusion towards the electrode surface. Simultaneously, specific COF-glyphosate binding catalyses the oxidative cleavage of the C–P bond and, together with pore nanoconfinement, enables sensitive glyphosate detection. Detailed sensing principles and selectiveness were scrutinized using DFT-based modelling. The proposed electrochemical method has a linear working range from 0.1 μM to 10 μM, a low limit of detection of 96 nM, and a limit of quantification of 320 nM. The elaborated sensing approach is viable for use in real sample matrices and tested for GLY determination in soil and water samples, without pretreatment, preparation, or purification. The results showed the practical usefulness of the sensor in the real sample analysis and suggested its suitability for possible out-of-laboratory sensing.",
publisher = "Elsevier",
journal = "Chemosphere",
title = "Direct glyphosate soil monitoring at the triazine-based covalent organic framework with the theoretical study of sensing principle",
volume = "341",
pages = "139930",
doi = "10.1016/j.chemosphere.2023.139930"
}
Knežević, S., Terzić-Jovanović, N., Vlahović, F., Ajdačić, V., Costache, V., Vidić, J., Opsenica, I.,& Stanković, D.. (2023). Direct glyphosate soil monitoring at the triazine-based covalent organic framework with the theoretical study of sensing principle. in Chemosphere
Elsevier., 341, 139930.
https://doi.org/10.1016/j.chemosphere.2023.139930
Knežević S, Terzić-Jovanović N, Vlahović F, Ajdačić V, Costache V, Vidić J, Opsenica I, Stanković D. Direct glyphosate soil monitoring at the triazine-based covalent organic framework with the theoretical study of sensing principle. in Chemosphere. 2023;341:139930.
doi:10.1016/j.chemosphere.2023.139930 .
Knežević, Sara, Terzić-Jovanović, Nataša, Vlahović, Filip, Ajdačić, Vladimir, Costache, Vlad, Vidić, Jasmina, Opsenica, Igor, Stanković, Dalibor, "Direct glyphosate soil monitoring at the triazine-based covalent organic framework with the theoretical study of sensing principle" in Chemosphere, 341 (2023):139930,
https://doi.org/10.1016/j.chemosphere.2023.139930 . .
3
3

Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts

Kokanović, Andrija; Ajdačić, Vladimir; Terzić Jovanović, Nataša; Stankić, Slavica; Opsenica, Igor

(American Chemical Society (ACS), 2023)

TY  - JOUR
AU  - Kokanović, Andrija
AU  - Ajdačić, Vladimir
AU  - Terzić Jovanović, Nataša
AU  - Stankić, Slavica
AU  - Opsenica, Igor
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7165
AB  - Herein, we report the synthesis and application of a highly active andversatile Pd/chemical vapor synthesis-ZnO (Pd/CVS-ZnO) catalytic system. The twosteppreparation of the catalyst includes chemical vapor synthesis (CVS) of ultrapureZnO nanotetrapods, followed by the liquid-phase in situ reduction of a Pd precursorand deposition of polycrystalline Pd nanoparticles (∼6 nm). The as-synthesized catalystwas characterized using standard instrumental techniques. The catalyst was successfullyapplied in four chemical reactions: Suzuki−Miyaura cross-coupling, reduction ofnitroarenes, decarbonylation, and hydrodebromination of aromatic compounds, ofwhich, the latter two are reported for the first time for the Pd/ZnO catalytic system.The catalyst showed excellent activity within a wide range of substrates, delivering the products in high yields (70−99%). Therecyclability of the Pd/CVS-ZnO catalyst was tested through two different approaches. First, the catalyst recyclability was examinedin all four reactions, reusing the catalyst up to four times in the Suzuki−Miyaura cross-coupling reaction, as well as the reduction of4-nitrobenzonitrile, without a significant loss of yield. Furthermore, the catalyst was successively used in three different reactions,showing a high degree of stability and delivering excellent product yields in all cases. In addition to its excellent activity, versatility,and stability, the Pd/CVS-ZnO catalytic system also exhibits excellent recyclability over consecutive runs, which makes it apromising candidate for future application in complex industrial processes.
PB  - American Chemical Society (ACS)
T2  - ACS Applied Nano Materials
T1  - Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts
VL  - 6
IS  - 17
SP  - 15820
EP  - 15828
DO  - 10.1021/acsanm.3c02743
ER  - 
@article{
author = "Kokanović, Andrija and Ajdačić, Vladimir and Terzić Jovanović, Nataša and Stankić, Slavica and Opsenica, Igor",
year = "2023",
abstract = "Herein, we report the synthesis and application of a highly active andversatile Pd/chemical vapor synthesis-ZnO (Pd/CVS-ZnO) catalytic system. The twosteppreparation of the catalyst includes chemical vapor synthesis (CVS) of ultrapureZnO nanotetrapods, followed by the liquid-phase in situ reduction of a Pd precursorand deposition of polycrystalline Pd nanoparticles (∼6 nm). The as-synthesized catalystwas characterized using standard instrumental techniques. The catalyst was successfullyapplied in four chemical reactions: Suzuki−Miyaura cross-coupling, reduction ofnitroarenes, decarbonylation, and hydrodebromination of aromatic compounds, ofwhich, the latter two are reported for the first time for the Pd/ZnO catalytic system.The catalyst showed excellent activity within a wide range of substrates, delivering the products in high yields (70−99%). Therecyclability of the Pd/CVS-ZnO catalyst was tested through two different approaches. First, the catalyst recyclability was examinedin all four reactions, reusing the catalyst up to four times in the Suzuki−Miyaura cross-coupling reaction, as well as the reduction of4-nitrobenzonitrile, without a significant loss of yield. Furthermore, the catalyst was successively used in three different reactions,showing a high degree of stability and delivering excellent product yields in all cases. In addition to its excellent activity, versatility,and stability, the Pd/CVS-ZnO catalytic system also exhibits excellent recyclability over consecutive runs, which makes it apromising candidate for future application in complex industrial processes.",
publisher = "American Chemical Society (ACS)",
journal = "ACS Applied Nano Materials",
title = "Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts",
volume = "6",
number = "17",
pages = "15820-15828",
doi = "10.1021/acsanm.3c02743"
}
Kokanović, A., Ajdačić, V., Terzić Jovanović, N., Stankić, S.,& Opsenica, I.. (2023). Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts. in ACS Applied Nano Materials
American Chemical Society (ACS)., 6(17), 15820-15828.
https://doi.org/10.1021/acsanm.3c02743
Kokanović A, Ajdačić V, Terzić Jovanović N, Stankić S, Opsenica I. Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts. in ACS Applied Nano Materials. 2023;6(17):15820-15828.
doi:10.1021/acsanm.3c02743 .
Kokanović, Andrija, Ajdačić, Vladimir, Terzić Jovanović, Nataša, Stankić, Slavica, Opsenica, Igor, "Pd Nanoparticles Supported on Ultrapure ZnO Nanopowders as Reusable Multipurpose Catalysts" in ACS Applied Nano Materials, 6, no. 17 (2023):15820-15828,
https://doi.org/10.1021/acsanm.3c02743 . .
2

Palladium on carbon in PEG-400/Cyclohexane: Recoverable and recyclable catalytic system for efficient decarbonylation of aldehydes

Terzić-Jovanović, Nataša; Ajdačić, Vladimir

(Serbian Chemical Society, 2022)

TY  - JOUR
AU  - Terzić-Jovanović, Nataša
AU  - Ajdačić, Vladimir
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5614
AB  - A simple methodology for the decarbonylation of aldehydes catalysed by commercially available palladium on carbon in a green two-solvent system is reported. Various aromatic, aliphatic and heteroaromatic aldehydes were transformed to the corresponding decarbonylated products in good yields. Product isolation from the reaction mixture is simple in practice, and the catalyst can be reused three times.
AB  - Развијена је једноставна метода за декарбониловање алдехида користећи комерцијално доступни паладијум на угљенику уз употребу зелених растварача. Различити ароматични, алифатични и хетероароматични алдехиди могу се трансформисати у декарбониловане производе у добром приносу и без настајања споредних производа. Производи се једноставно изолоју из реакционе смеше, а исти катализатор се може употребити још три пута без значајног смањења приноса.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Palladium on carbon in PEG-400/Cyclohexane: Recoverable and recyclable catalytic system for efficient decarbonylation of aldehydes
T1  - Паладијум на угљенику у peg-400/циклохексану: каталитички систем kojи се може рециклирати и поново употребити за ефикасно декарбониловање алдехида
VL  - 87
IS  - 6
SP  - 669
EP  - 675
DO  - 10.2298/JSC220128024T
ER  - 
@article{
author = "Terzić-Jovanović, Nataša and Ajdačić, Vladimir",
year = "2022",
abstract = "A simple methodology for the decarbonylation of aldehydes catalysed by commercially available palladium on carbon in a green two-solvent system is reported. Various aromatic, aliphatic and heteroaromatic aldehydes were transformed to the corresponding decarbonylated products in good yields. Product isolation from the reaction mixture is simple in practice, and the catalyst can be reused three times., Развијена је једноставна метода за декарбониловање алдехида користећи комерцијално доступни паладијум на угљенику уз употребу зелених растварача. Различити ароматични, алифатични и хетероароматични алдехиди могу се трансформисати у декарбониловане производе у добром приносу и без настајања споредних производа. Производи се једноставно изолоју из реакционе смеше, а исти катализатор се може употребити још три пута без значајног смањења приноса.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Palladium on carbon in PEG-400/Cyclohexane: Recoverable and recyclable catalytic system for efficient decarbonylation of aldehydes, Паладијум на угљенику у peg-400/циклохексану: каталитички систем kojи се може рециклирати и поново употребити за ефикасно декарбониловање алдехида",
volume = "87",
number = "6",
pages = "669-675",
doi = "10.2298/JSC220128024T"
}
Terzić-Jovanović, N.,& Ajdačić, V.. (2022). Palladium on carbon in PEG-400/Cyclohexane: Recoverable and recyclable catalytic system for efficient decarbonylation of aldehydes. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 87(6), 669-675.
https://doi.org/10.2298/JSC220128024T
Terzić-Jovanović N, Ajdačić V. Palladium on carbon in PEG-400/Cyclohexane: Recoverable and recyclable catalytic system for efficient decarbonylation of aldehydes. in Journal of the Serbian Chemical Society. 2022;87(6):669-675.
doi:10.2298/JSC220128024T .
Terzić-Jovanović, Nataša, Ajdačić, Vladimir, "Palladium on carbon in PEG-400/Cyclohexane: Recoverable and recyclable catalytic system for efficient decarbonylation of aldehydes" in Journal of the Serbian Chemical Society, 87, no. 6 (2022):669-675,
https://doi.org/10.2298/JSC220128024T . .
1

Supporting information for: "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines"

Nikolić, Andrea; Stanić, Jelena; Zlatar, Matija; Gruden, Maja; Anđelković, Boban; Selaković, Života; Ajdačić, Vladimir; Opsenica, Igor

(American Chemical Society (ACS), 2021)

TY  - DATA
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4444
AB  - Copies of 1H and 13C NMR spectra for the synthesized compounds; Extended computational results, and total electronic energies, number of imaginary frequencies;  Cartesian coordinates of all structures.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - Supporting information for: "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines"
DO  - 10.1021/acs.joc.1c00282.s001
ER  - 
@misc{
author = "Nikolić, Andrea and Stanić, Jelena and Zlatar, Matija and Gruden, Maja and Anđelković, Boban and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
abstract = "Copies of 1H and 13C NMR spectra for the synthesized compounds; Extended computational results, and total electronic energies, number of imaginary frequencies;  Cartesian coordinates of all structures.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "Supporting information for: "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines"",
doi = "10.1021/acs.joc.1c00282.s001"
}
Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I.. (2021). Supporting information for: "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines". in The Journal of Organic Chemistry
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.joc.1c00282.s001
Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković B, Selaković Ž, Ajdačić V, Opsenica I. Supporting information for: "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines". in The Journal of Organic Chemistry. 2021;.
doi:10.1021/acs.joc.1c00282.s001 .
Nikolić, Andrea, Stanić, Jelena, Zlatar, Matija, Gruden, Maja, Anđelković, Boban, Selaković, Života, Ajdačić, Vladimir, Opsenica, Igor, "Supporting information for: "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines"" in The Journal of Organic Chemistry (2021),
https://doi.org/10.1021/acs.joc.1c00282.s001 . .

Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines

Nikolić, Andrea; Stanić, Jelena; Zlatar, Matija; Gruden, Maja; Anđelković, Boban; Selaković, Života; Ajdačić, Vladimir; Opsenica, Igor

(American Chemical Society (ACS), 2021)

TY  - JOUR
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4443
AB  - The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines
VL  - 86
IS  - 6
SP  - 4794
EP  - 4803
DO  - 10.1021/acs.joc.1c00282
ER  - 
@article{
author = "Nikolić, Andrea and Stanić, Jelena and Zlatar, Matija and Gruden, Maja and Anđelković, Boban and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
abstract = "The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines",
volume = "86",
number = "6",
pages = "4794-4803",
doi = "10.1021/acs.joc.1c00282"
}
Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I.. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. in The Journal of Organic Chemistry
American Chemical Society (ACS)., 86(6), 4794-4803.
https://doi.org/10.1021/acs.joc.1c00282
Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković B, Selaković Ž, Ajdačić V, Opsenica I. Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. in The Journal of Organic Chemistry. 2021;86(6):4794-4803.
doi:10.1021/acs.joc.1c00282 .
Nikolić, Andrea, Stanić, Jelena, Zlatar, Matija, Gruden, Maja, Anđelković, Boban, Selaković, Života, Ajdačić, Vladimir, Opsenica, Igor, "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines" in The Journal of Organic Chemistry, 86, no. 6 (2021):4794-4803,
https://doi.org/10.1021/acs.joc.1c00282 . .
10
6
2
6

Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines

Nikolić, Andrea; Stanić, Jelena; Zlatar, Matija; Gruden, Maja; Anđelković, Boban; Selaković, Života; Ajdačić, Vladimir; Opsenica, Igor

(American Chemical Society (ACS), 2021)

TY  - JOUR
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4431
AB  - The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines
VL  - 86
IS  - 6
SP  - 4794
EP  - 4803
DO  - 10.1021/acs.joc.1c00282
ER  - 
@article{
author = "Nikolić, Andrea and Stanić, Jelena and Zlatar, Matija and Gruden, Maja and Anđelković, Boban and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
abstract = "The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines",
volume = "86",
number = "6",
pages = "4794-4803",
doi = "10.1021/acs.joc.1c00282"
}
Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I.. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. in The Journal of Organic Chemistry
American Chemical Society (ACS)., 86(6), 4794-4803.
https://doi.org/10.1021/acs.joc.1c00282
Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković B, Selaković Ž, Ajdačić V, Opsenica I. Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. in The Journal of Organic Chemistry. 2021;86(6):4794-4803.
doi:10.1021/acs.joc.1c00282 .
Nikolić, Andrea, Stanić, Jelena, Zlatar, Matija, Gruden, Maja, Anđelković, Boban, Selaković, Života, Ajdačić, Vladimir, Opsenica, Igor, "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines" in The Journal of Organic Chemistry, 86, no. 6 (2021):4794-4803,
https://doi.org/10.1021/acs.joc.1c00282 . .
10
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Antibacterial and antifungal properties of guanylhydrazones

Ajdačić, Vladimir; Lazić, Jelena; Mojicevic, Marija; Šegan, Sandra; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Serbian Chemical Soc, Belgrade, 2017)

TY  - JOUR
AU  - Ajdačić, Vladimir
AU  - Lazić, Jelena
AU  - Mojicevic, Marija
AU  - Šegan, Sandra
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2138
AB  - A series of novel guanylhydrazones were designed, synthesized and characterized. All the compounds were screened for their antibacterial and antifungal activity. Compounds 26 and 27 showed excellent antibacterial activities against Staphylococcus aureus ATCC 25923 and Micrococcus luteus ATCC 379 with minimal inhibitory concentrations of 4 ae g mL(-1), and good antifungal activity against Candida parapsilosis ATCC 22019. These results suggested that the selected guanylhydrazones could serve as promising leads for improved antimicrobial development.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Antibacterial and antifungal properties of guanylhydrazones
VL  - 82
IS  - 6
SP  - 641
EP  - 649
DO  - 10.2298/JSC170213033A
ER  - 
@article{
author = "Ajdačić, Vladimir and Lazić, Jelena and Mojicevic, Marija and Šegan, Sandra and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2017",
abstract = "A series of novel guanylhydrazones were designed, synthesized and characterized. All the compounds were screened for their antibacterial and antifungal activity. Compounds 26 and 27 showed excellent antibacterial activities against Staphylococcus aureus ATCC 25923 and Micrococcus luteus ATCC 379 with minimal inhibitory concentrations of 4 ae g mL(-1), and good antifungal activity against Candida parapsilosis ATCC 22019. These results suggested that the selected guanylhydrazones could serve as promising leads for improved antimicrobial development.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Antibacterial and antifungal properties of guanylhydrazones",
volume = "82",
number = "6",
pages = "641-649",
doi = "10.2298/JSC170213033A"
}
Ajdačić, V., Lazić, J., Mojicevic, M., Šegan, S., Nikodinović-Runić, J.,& Opsenica, I.. (2017). Antibacterial and antifungal properties of guanylhydrazones. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 82(6), 641-649.
https://doi.org/10.2298/JSC170213033A
Ajdačić V, Lazić J, Mojicevic M, Šegan S, Nikodinović-Runić J, Opsenica I. Antibacterial and antifungal properties of guanylhydrazones. in Journal of the Serbian Chemical Society. 2017;82(6):641-649.
doi:10.2298/JSC170213033A .
Ajdačić, Vladimir, Lazić, Jelena, Mojicevic, Marija, Šegan, Sandra, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Antibacterial and antifungal properties of guanylhydrazones" in Journal of the Serbian Chemical Society, 82, no. 6 (2017):641-649,
https://doi.org/10.2298/JSC170213033A . .
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3

Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine

Ajdačić, Vladimir; Stepanović, Stepan; Zlatović, Mario; Gruden, Maja; Opsenica, Igor

(Georg Thieme Verlag Kg, Stuttgart, 2016)

TY  - JOUR
AU  - Ajdačić, Vladimir
AU  - Stepanović, Stepan
AU  - Zlatović, Mario
AU  - Gruden, Maja
AU  - Opsenica, Igor
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1951
AB  - The decarbonylative dibromination of 2-thiophenecarboxaldehyde derivatives with bromine under mild conditions is developed. The mechanism for the decarbonylation is investigated by experimental and instrumental techniques and is extended by a computational study. Alongside removal of the formyl group, this method enables functionalization of the starting compounds in a single reaction step, which can be further exploited for the synthesis of 2,5-diaryl-3-bromothiophenes and 2,3,5-triarylthiophenes.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis
T1  - Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine
VL  - 48
IS  - 24
SP  - 4423
EP  - 4430
DO  - 10.1055/s-0035-1562615
ER  - 
@article{
author = "Ajdačić, Vladimir and Stepanović, Stepan and Zlatović, Mario and Gruden, Maja and Opsenica, Igor",
year = "2016",
abstract = "The decarbonylative dibromination of 2-thiophenecarboxaldehyde derivatives with bromine under mild conditions is developed. The mechanism for the decarbonylation is investigated by experimental and instrumental techniques and is extended by a computational study. Alongside removal of the formyl group, this method enables functionalization of the starting compounds in a single reaction step, which can be further exploited for the synthesis of 2,5-diaryl-3-bromothiophenes and 2,3,5-triarylthiophenes.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis",
title = "Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine",
volume = "48",
number = "24",
pages = "4423-4430",
doi = "10.1055/s-0035-1562615"
}
Ajdačić, V., Stepanović, S., Zlatović, M., Gruden, M.,& Opsenica, I.. (2016). Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine. in Synthesis
Georg Thieme Verlag Kg, Stuttgart., 48(24), 4423-4430.
https://doi.org/10.1055/s-0035-1562615
Ajdačić V, Stepanović S, Zlatović M, Gruden M, Opsenica I. Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine. in Synthesis. 2016;48(24):4423-4430.
doi:10.1055/s-0035-1562615 .
Ajdačić, Vladimir, Stepanović, Stepan, Zlatović, Mario, Gruden, Maja, Opsenica, Igor, "Decarbonylative Dibromination of 5-Phenylthiophene-2-carbaldehyde with Bromine" in Synthesis, 48, no. 24 (2016):4423-4430,
https://doi.org/10.1055/s-0035-1562615 . .
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