TY  - JOUR
AU  - Stojiljkovic, Ivana N.
AU  - Rancic, Milica P.
AU  - Marinković, Aleksandar
AU  - Cvijetić, Ilija
AU  - Milcic, Milos K.
PY  - 2021
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4891
AB  - Electronic interactions in donor-pi-linker-acceptor systems with barbituric acid as an electron acceptor and possible electron donor were investigated to screen promising candidates with a push-pull character based on experimental and quantum chemical studies. The tautomeric properties of 5-benzylidenebarbituric acid derivatives were studied with NMR spectra, spectrophotometric determination of the pKa values, and quantum chemical calculations. Linear solvation energy relationships (LSER) and linear free energy relationships (LFER) were applied to the spectral data - UV frequencies and C-13 NMR chemical shifts. The experimental studies of the nature of the ground and excited state of investigated compounds were successfully interpreted using a computational chemistry approach including ab initio MP2 geometry optimization and time-dependent DFT calculations of excited states. Quantification of the push-pull character of barbituric acid derivatives was performed by the (CNMR)-C-13 chemical shift differences, Mayer pi bond order analysis, hole-electron distribution analysis, and calculations of intramolecular charge transfer (ICT) indices. The results obtained show, that when coupled with a strong electron-donor, barbituric acid can act as the electron-acceptor in push-pull systems, and when coupled with a strong electron-acceptor, barbituric acid can act as the weak electron-donor.
T2  - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
T1  - Assessing the potential of para-donor and para-acceptor substituted 5-benzylidenebarbituric acid derivatives as push-pull electronic systems: Experimental and quantum chemical study
VL  - 253
DO  - 10.1016/j.saa.2021.119576
ER  - 

@article{
author = "Stojiljkovic, Ivana N. and Rancic, Milica P. and Marinković, Aleksandar and Cvijetić, Ilija and Milcic, Milos K.",
year = "2021",
abstract = "Electronic interactions in donor-pi-linker-acceptor systems with barbituric acid as an electron acceptor and possible electron donor were investigated to screen promising candidates with a push-pull character based on experimental and quantum chemical studies. The tautomeric properties of 5-benzylidenebarbituric acid derivatives were studied with NMR spectra, spectrophotometric determination of the pKa values, and quantum chemical calculations. Linear solvation energy relationships (LSER) and linear free energy relationships (LFER) were applied to the spectral data - UV frequencies and C-13 NMR chemical shifts. The experimental studies of the nature of the ground and excited state of investigated compounds were successfully interpreted using a computational chemistry approach including ab initio MP2 geometry optimization and time-dependent DFT calculations of excited states. Quantification of the push-pull character of barbituric acid derivatives was performed by the (CNMR)-C-13 chemical shift differences, Mayer pi bond order analysis, hole-electron distribution analysis, and calculations of intramolecular charge transfer (ICT) indices. The results obtained show, that when coupled with a strong electron-donor, barbituric acid can act as the electron-acceptor in push-pull systems, and when coupled with a strong electron-acceptor, barbituric acid can act as the weak electron-donor.",
journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy",
title = "Assessing the potential of para-donor and para-acceptor substituted 5-benzylidenebarbituric acid derivatives as push-pull electronic systems: Experimental and quantum chemical study",
volume = "253",
doi = "10.1016/j.saa.2021.119576"
}

Stojiljkovic, I. N., Rancic, M. P., Marinković, A., Cvijetić, I.,& Milcic, M. K.. (2021). Assessing the potential of para-donor and para-acceptor substituted 5-benzylidenebarbituric acid derivatives as push-pull electronic systems: Experimental and quantum chemical study. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 253.
https://doi.org/10.1016/j.saa.2021.119576

Stojiljkovic IN, Rancic MP, Marinković A, Cvijetić I, Milcic MK. Assessing the potential of para-donor and para-acceptor substituted 5-benzylidenebarbituric acid derivatives as push-pull electronic systems: Experimental and quantum chemical study. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 2021;253.
doi:10.1016/j.saa.2021.119576 .

Stojiljkovic, Ivana N., Rancic, Milica P., Marinković, Aleksandar, Cvijetić, Ilija, Milcic, Milos K., "Assessing the potential of para-donor and para-acceptor substituted 5-benzylidenebarbituric acid derivatives as push-pull electronic systems: Experimental and quantum chemical study" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 253 (2021),
https://doi.org/10.1016/j.saa.2021.119576 . .

TY  - JOUR
AU  - Popov-Pergal, Katarina M.
AU  - Poleti, Dejan
AU  - Rancic, Milica P.
AU  - Meden, Antun
AU  - Pergal, Marija
PY  - 2010
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5616
AB  - The derivatives of 5-substituted-2,4-thiazolidinedione have a broad spectrum of biological activities. In this article, new 5-(arylidene)-3-(4-methylbenzoyl)thiayolidine-2,4-diones 3a-k, with arylidene groups such as 4-phenylbenzylidene 3a, 3,4-dimethoxybenzylidene 3b, 2-hydroxybenzylidene 3c, 4-ethoxybenzylidene 3d, 5-methyl-2-furfurylidene 3e, 4-dimethylaminobenzylidene 3f, 1-naphthylidene 3g, 3,4-methylenedioxybenzylidene 3h, 4-benzyloxybenzylidene 3i, benzylidene 3j, and 4-methoxybenzylidene 3k, were synthesized by direct acylation of alkali metal salts of 5-arylidene-2,4-thiazolidinediones with 4-methylbenzoylchloride. Their structures were confirmed by elemental analysis, IR, (1)H NMR and MS spectroscopy. In addition, crystal structure of the compound 3d was determined using single-crystal X-ray diffraction data.
PB  - Wiley-Blackwell Publishing, Inc, Malden
T2  - Journal of Heterocyclic Chemistry
T1  - Synthesis and Structure of New 5-(Arylidene)-3-(4-methylbenzoyl)thiazolidine-2,4-diones
EP  - 228
IS  - 1
SP  - 224
VL  - 47
DO  - 10.1002/jhet.288
ER  - 

@article{
author = "Popov-Pergal, Katarina M. and Poleti, Dejan and Rancic, Milica P. and Meden, Antun and Pergal, Marija",
year = "2010",
abstract = "The derivatives of 5-substituted-2,4-thiazolidinedione have a broad spectrum of biological activities. In this article, new 5-(arylidene)-3-(4-methylbenzoyl)thiayolidine-2,4-diones 3a-k, with arylidene groups such as 4-phenylbenzylidene 3a, 3,4-dimethoxybenzylidene 3b, 2-hydroxybenzylidene 3c, 4-ethoxybenzylidene 3d, 5-methyl-2-furfurylidene 3e, 4-dimethylaminobenzylidene 3f, 1-naphthylidene 3g, 3,4-methylenedioxybenzylidene 3h, 4-benzyloxybenzylidene 3i, benzylidene 3j, and 4-methoxybenzylidene 3k, were synthesized by direct acylation of alkali metal salts of 5-arylidene-2,4-thiazolidinediones with 4-methylbenzoylchloride. Their structures were confirmed by elemental analysis, IR, (1)H NMR and MS spectroscopy. In addition, crystal structure of the compound 3d was determined using single-crystal X-ray diffraction data.",
publisher = "Wiley-Blackwell Publishing, Inc, Malden",
journal = "Journal of Heterocyclic Chemistry",
title = "Synthesis and Structure of New 5-(Arylidene)-3-(4-methylbenzoyl)thiazolidine-2,4-diones",
pages = "228-224",
number = "1",
volume = "47",
doi = "10.1002/jhet.288"
}

Popov-Pergal, K. M., Poleti, D., Rancic, M. P., Meden, A.,& Pergal, M.. (2010). Synthesis and Structure of New 5-(Arylidene)-3-(4-methylbenzoyl)thiazolidine-2,4-diones. in Journal of Heterocyclic Chemistry
Wiley-Blackwell Publishing, Inc, Malden., 47(1), 224-228.
https://doi.org/10.1002/jhet.288

Popov-Pergal KM, Poleti D, Rancic MP, Meden A, Pergal M. Synthesis and Structure of New 5-(Arylidene)-3-(4-methylbenzoyl)thiazolidine-2,4-diones. in Journal of Heterocyclic Chemistry. 2010;47(1):224-228.
doi:10.1002/jhet.288 .

Popov-Pergal, Katarina M., Poleti, Dejan, Rancic, Milica P., Meden, Antun, Pergal, Marija, "Synthesis and Structure of New 5-(Arylidene)-3-(4-methylbenzoyl)thiazolidine-2,4-diones" in Journal of Heterocyclic Chemistry, 47, no. 1 (2010):224-228,
https://doi.org/10.1002/jhet.288 . .