TY  - JOUR
AU  - Ajaj, Ismail
AU  - Assaleh, Fathi H.
AU  - Markovski, Jasmina
AU  - Rančić, Milica
AU  - Brković, Danijela
AU  - Milcić, Miloš
AU  - Marinković, Aleksandar D.
PY  - 2019
UR  - https://omorika.sfb.bg.ac.rs/handle/123456789/1020
AB  - The state of the tautomeric equilibria of eleven arylazo pyridone dyes was evaluated from UV-Vis absorption spectra with the aid of the quantum mechanical modeling. NMR analysis and theoretical calculations, by using PCM/omega B97X-D/6-311G(d,p) method, confirmed that prepared compounds exist mainly in Hydrazo form. Internal hydrogen bonding in Hydrazo tautomer, analyzed by AIM topological analysis and total electron density at the bond critical point (BCP), confirmed a presence of strong hydrogen bond which contributes to higher stability of Hydrazo form. Linear solvation energy relationships (LSERs) rationalized solvent influence on solvatochromism of all compounds in Hydrazo form and K-T by using Kamlet-Taft model. Linear free energy relationships (LFERs) were applied to the substituent-inducedNMR chemical shifts (SCS) using SSP (single substituent parameter) and DSP (dual substituent parameter) model. Density plots over the highest occupied (HOMO) and lowest unoccupied molecular orbitals (LUMO) energy surface provide information on the charge transfer during excitation. The molecular electrostatic potential (MEP) surface map was plotted over the optimized geometry of the molecules in order to visualize electron density distribution and explain origin of solvent/solute interactions.
PB  - Elsevier
T2  - Arabian Journal of Chemistry
T1  - Solvatochromism and azo-hydrazo tautomerism of novel arylazo pyridone dyes: Experimental and quantum chemical study
EP  - 3478
IS  - 8
SP  - 3463
VL  - 12
UR  - conv_2390
ER  - 

@article{
author = "Ajaj, Ismail and Assaleh, Fathi H. and Markovski, Jasmina and Rančić, Milica and Brković, Danijela and Milcić, Miloš and Marinković, Aleksandar D.",
year = "2019",
abstract = "The state of the tautomeric equilibria of eleven arylazo pyridone dyes was evaluated from UV-Vis absorption spectra with the aid of the quantum mechanical modeling. NMR analysis and theoretical calculations, by using PCM/omega B97X-D/6-311G(d,p) method, confirmed that prepared compounds exist mainly in Hydrazo form. Internal hydrogen bonding in Hydrazo tautomer, analyzed by AIM topological analysis and total electron density at the bond critical point (BCP), confirmed a presence of strong hydrogen bond which contributes to higher stability of Hydrazo form. Linear solvation energy relationships (LSERs) rationalized solvent influence on solvatochromism of all compounds in Hydrazo form and K-T by using Kamlet-Taft model. Linear free energy relationships (LFERs) were applied to the substituent-inducedNMR chemical shifts (SCS) using SSP (single substituent parameter) and DSP (dual substituent parameter) model. Density plots over the highest occupied (HOMO) and lowest unoccupied molecular orbitals (LUMO) energy surface provide information on the charge transfer during excitation. The molecular electrostatic potential (MEP) surface map was plotted over the optimized geometry of the molecules in order to visualize electron density distribution and explain origin of solvent/solute interactions.",
publisher = "Elsevier",
journal = "Arabian Journal of Chemistry",
title = "Solvatochromism and azo-hydrazo tautomerism of novel arylazo pyridone dyes: Experimental and quantum chemical study",
pages = "3478-3463",
number = "8",
volume = "12",
url = "conv_2390"
}

Ajaj, I., Assaleh, F. H., Markovski, J., Rančić, M., Brković, D., Milcić, M.,& Marinković, A. D.. (2019). Solvatochromism and azo-hydrazo tautomerism of novel arylazo pyridone dyes: Experimental and quantum chemical study. in Arabian Journal of Chemistry
Elsevier., 12(8), 3463-3478.
conv_2390

Ajaj I, Assaleh FH, Markovski J, Rančić M, Brković D, Milcić M, Marinković AD. Solvatochromism and azo-hydrazo tautomerism of novel arylazo pyridone dyes: Experimental and quantum chemical study. in Arabian Journal of Chemistry. 2019;12(8):3463-3478.
conv_2390 .

Ajaj, Ismail, Assaleh, Fathi H., Markovski, Jasmina, Rančić, Milica, Brković, Danijela, Milcić, Miloš, Marinković, Aleksandar D., "Solvatochromism and azo-hydrazo tautomerism of novel arylazo pyridone dyes: Experimental and quantum chemical study" in Arabian Journal of Chemistry, 12, no. 8 (2019):3463-3478,
conv_2390 .

TY  - JOUR
AU  - Prlainović, Nevena
AU  - Rančić, Milica
AU  - Stojiljković, Ivana
AU  - Nikolić, Jasmina B.
AU  - Drmanić, Saša Z.
AU  - Ajaj, Ismail
AU  - Marinković, Aleksandar D.
PY  - 2018
UR  - https://omorika.sfb.bg.ac.rs/handle/123456789/923
AB  - The substituent and solvent effects on solvatochromism in 3-[(4-substituted) phenylamino] isobenzofuran-1(3H)-ones were studied using experimental and theoretical methodologies. The effect of specific and non-specific solvent-solute interactions on the shifts of UV-Vis absorption maxima were evaluated using the Kamlet-Taft and Catalan solvent parameter sets. The experimental results were studied by density functional theory (DT) and time-dependent density functional theory (TD-DFT). The HOMO/LUMO energies (EHOMO/ELUMO) and energy gap (E-gap) values, as well as the mechanism of electronic excitations and the changes in the electron density distribution in both ground and excited states of the investigated molecules were studied by calculation in the gas phase. The electronic excitations were calculated by the TD-DFT method in the solvent methanol. It was found that both substituents and solvents influence the degree of p-electron conjugation of the synthesized molecules and affect the intramolecular charge transfer character.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Experimental and theoretical study on solvent and substituent effects on the intramolecular charge transfer in 3-[(4-substituted)phenylamino]isobenzofuran-1( 3H )-ones
EP  - 155
IS  - 2
SP  - 139
VL  - 83
DO  - 10.2298/JSC170408003P
UR  - conv_1333
ER  - 

@article{
author = "Prlainović, Nevena and Rančić, Milica and Stojiljković, Ivana and Nikolić, Jasmina B. and Drmanić, Saša Z. and Ajaj, Ismail and Marinković, Aleksandar D.",
year = "2018",
abstract = "The substituent and solvent effects on solvatochromism in 3-[(4-substituted) phenylamino] isobenzofuran-1(3H)-ones were studied using experimental and theoretical methodologies. The effect of specific and non-specific solvent-solute interactions on the shifts of UV-Vis absorption maxima were evaluated using the Kamlet-Taft and Catalan solvent parameter sets. The experimental results were studied by density functional theory (DT) and time-dependent density functional theory (TD-DFT). The HOMO/LUMO energies (EHOMO/ELUMO) and energy gap (E-gap) values, as well as the mechanism of electronic excitations and the changes in the electron density distribution in both ground and excited states of the investigated molecules were studied by calculation in the gas phase. The electronic excitations were calculated by the TD-DFT method in the solvent methanol. It was found that both substituents and solvents influence the degree of p-electron conjugation of the synthesized molecules and affect the intramolecular charge transfer character.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Experimental and theoretical study on solvent and substituent effects on the intramolecular charge transfer in 3-[(4-substituted)phenylamino]isobenzofuran-1( 3H )-ones",
pages = "155-139",
number = "2",
volume = "83",
doi = "10.2298/JSC170408003P",
url = "conv_1333"
}

Prlainović, N., Rančić, M., Stojiljković, I., Nikolić, J. B., Drmanić, S. Z., Ajaj, I.,& Marinković, A. D.. (2018). Experimental and theoretical study on solvent and substituent effects on the intramolecular charge transfer in 3-[(4-substituted)phenylamino]isobenzofuran-1( 3H )-ones. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 83(2), 139-155.
https://doi.org/10.2298/JSC170408003P
conv_1333

Prlainović N, Rančić M, Stojiljković I, Nikolić JB, Drmanić SZ, Ajaj I, Marinković AD. Experimental and theoretical study on solvent and substituent effects on the intramolecular charge transfer in 3-[(4-substituted)phenylamino]isobenzofuran-1( 3H )-ones. in Journal of the Serbian Chemical Society. 2018;83(2):139-155.
doi:10.2298/JSC170408003P
conv_1333 .

Prlainović, Nevena, Rančić, Milica, Stojiljković, Ivana, Nikolić, Jasmina B., Drmanić, Saša Z., Ajaj, Ismail, Marinković, Aleksandar D., "Experimental and theoretical study on solvent and substituent effects on the intramolecular charge transfer in 3-[(4-substituted)phenylamino]isobenzofuran-1( 3H )-ones" in Journal of the Serbian Chemical Society, 83, no. 2 (2018):139-155,
https://doi.org/10.2298/JSC170408003P .,
conv_1333 .

TY  - JOUR
AU  - Ajaj, Ismail
AU  - Markovski, Jasmina
AU  - Rančić, Milica
AU  - Mijin, Dusan
AU  - Milcić, Miloš
AU  - Jovanović, Maja
AU  - Marinković, Aleksandar
PY  - 2015
UR  - https://omorika.sfb.bg.ac.rs/handle/123456789/651
AB  - The state of the tautomeric equilibria of 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles, 2-PY/6-PY, was evaluated using experimental and theoretical methodology. The experimental data were interpreted with the aid of time-dependent density functional (TD-DFT) method. Electron charge density was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Bader's analysis. Linear solvation energy relationships (LSER) rationalized solvent influence on tautomeric equilibrium. Linear free energy relationships (LFERs) were applied to the substituent-induced NMR chemical shifts (SCS) using SSP (single substituent parameter) and DSP (dual substituent parameter) model. Theoretical calculations and obtained correlations gave insight into the influence of molecular conformation on the transmission of substituent electronic effects, as well as on different solvent solute interactions, and the state of tautomeric equilibrium.
T2  - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
T1  - Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study
EP  - 585
SP  - 575
VL  - 150
DO  - 10.1016/j.saa.2015.05.055
UR  - conv_1172
ER  - 

@article{
author = "Ajaj, Ismail and Markovski, Jasmina and Rančić, Milica and Mijin, Dusan and Milcić, Miloš and Jovanović, Maja and Marinković, Aleksandar",
year = "2015",
abstract = "The state of the tautomeric equilibria of 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles, 2-PY/6-PY, was evaluated using experimental and theoretical methodology. The experimental data were interpreted with the aid of time-dependent density functional (TD-DFT) method. Electron charge density was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Bader's analysis. Linear solvation energy relationships (LSER) rationalized solvent influence on tautomeric equilibrium. Linear free energy relationships (LFERs) were applied to the substituent-induced NMR chemical shifts (SCS) using SSP (single substituent parameter) and DSP (dual substituent parameter) model. Theoretical calculations and obtained correlations gave insight into the influence of molecular conformation on the transmission of substituent electronic effects, as well as on different solvent solute interactions, and the state of tautomeric equilibrium.",
journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy",
title = "Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study",
pages = "585-575",
volume = "150",
doi = "10.1016/j.saa.2015.05.055",
url = "conv_1172"
}

Ajaj, I., Markovski, J., Rančić, M., Mijin, D., Milcić, M., Jovanović, M.,& Marinković, A.. (2015). Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 150, 575-585.
https://doi.org/10.1016/j.saa.2015.05.055
conv_1172

Ajaj I, Markovski J, Rančić M, Mijin D, Milcić M, Jovanović M, Marinković A. Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 2015;150:575-585.
doi:10.1016/j.saa.2015.05.055
conv_1172 .

Ajaj, Ismail, Markovski, Jasmina, Rančić, Milica, Mijin, Dusan, Milcić, Miloš, Jovanović, Maja, Marinković, Aleksandar, "Solvent and structural effects in tautomeric 2(6)-hydroxy-4-methyl-6(2)-oxo-1-(substituted phenyl)-1,2(1,6)-dihydropyridine-3-carbonitriles: UV, NMR and quantum chemical study" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 150 (2015):575-585,
https://doi.org/10.1016/j.saa.2015.05.055 .,
conv_1172 .

TY  - JOUR
AU  - Rančić, Milica
AU  - Trisović, Nemanja
AU  - Milcić, Miloš K.
AU  - Ajaj, Ismail
AU  - Marinković, Aleksandar D.
PY  - 2013
UR  - https://omorika.sfb.bg.ac.rs/handle/123456789/499
AB  - The electronic structure of 5-arylidene-2,4-thiazolidinediones has been studied by using experimental and theoretical methodology. The theoretical calculations of the investigated 5-arylidene-2,4-thiazolidinediones have been performed by the use of quantum chemical methods. The calculated C-13 NMR chemical shifts and NBO atomic charges provide an insight into the influence of such a structure on the transmission of electronic substituent effects. Linear free energy relationships (LFERs) have been further applied to their C-13 NMR chemical shifts. The correlation analyses for the substituent-induced chemical shifts (SCS) have been performed with sigma using SSP (single substituent parameter), field (sigma(F)) and resonance (sigma(R)) parameters using DSP (dual substituent parameter), as well as the Yukawa-Tsuno model. The presented correlations account satisfactorily for the polar and resonance substituent effects operative at C-beta. and C-7 carbons, while reverse substituent effect was found for C-alpha. The comparison of correlation results for the investigated molecules with those obtained for seven structurally related styrene series has indicated that specific cross-interaction of phenyl substituent and groups attached at C-alpha carbon causes increased sensitivity of SCS C-beta to the resonance effect with increasing of electron-accepting capabilities of the group present at C-beta.
T2  - Journal of Molecular Structure
T1  - Experimental and theoretical study of substituent effect on 13 C NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones
EP  - 68
SP  - 59
VL  - 1049
DO  - 10.1016/j.molstruc.2013.06.027
UR  - conv_919
ER  - 

@article{
author = "Rančić, Milica and Trisović, Nemanja and Milcić, Miloš K. and Ajaj, Ismail and Marinković, Aleksandar D.",
year = "2013",
abstract = "The electronic structure of 5-arylidene-2,4-thiazolidinediones has been studied by using experimental and theoretical methodology. The theoretical calculations of the investigated 5-arylidene-2,4-thiazolidinediones have been performed by the use of quantum chemical methods. The calculated C-13 NMR chemical shifts and NBO atomic charges provide an insight into the influence of such a structure on the transmission of electronic substituent effects. Linear free energy relationships (LFERs) have been further applied to their C-13 NMR chemical shifts. The correlation analyses for the substituent-induced chemical shifts (SCS) have been performed with sigma using SSP (single substituent parameter), field (sigma(F)) and resonance (sigma(R)) parameters using DSP (dual substituent parameter), as well as the Yukawa-Tsuno model. The presented correlations account satisfactorily for the polar and resonance substituent effects operative at C-beta. and C-7 carbons, while reverse substituent effect was found for C-alpha. The comparison of correlation results for the investigated molecules with those obtained for seven structurally related styrene series has indicated that specific cross-interaction of phenyl substituent and groups attached at C-alpha carbon causes increased sensitivity of SCS C-beta to the resonance effect with increasing of electron-accepting capabilities of the group present at C-beta.",
journal = "Journal of Molecular Structure",
title = "Experimental and theoretical study of substituent effect on 13 C NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones",
pages = "68-59",
volume = "1049",
doi = "10.1016/j.molstruc.2013.06.027",
url = "conv_919"
}

Rančić, M., Trisović, N., Milcić, M. K., Ajaj, I.,& Marinković, A. D.. (2013). Experimental and theoretical study of substituent effect on 13 C NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones. in Journal of Molecular Structure, 1049, 59-68.
https://doi.org/10.1016/j.molstruc.2013.06.027
conv_919

Rančić M, Trisović N, Milcić MK, Ajaj I, Marinković AD. Experimental and theoretical study of substituent effect on 13 C NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones. in Journal of Molecular Structure. 2013;1049:59-68.
doi:10.1016/j.molstruc.2013.06.027
conv_919 .

Rančić, Milica, Trisović, Nemanja, Milcić, Miloš K., Ajaj, Ismail, Marinković, Aleksandar D., "Experimental and theoretical study of substituent effect on 13 C NMR chemical shifts of 5-arylidene-2,4-thiazolidinediones" in Journal of Molecular Structure, 1049 (2013):59-68,
https://doi.org/10.1016/j.molstruc.2013.06.027 .,
conv_919 .