Experimental and theoretical study on solvent and substituent effects on the intramolecular charge transfer in 3-[(4-substituted)phenylamino]isobenzofuran-1(3H)-ones
Authors
Prlainović, NevenaRančić, Milica
Stojiljković, Ivana
Nikolić, Jasmina
Drmanić, Saša
Ajaj, Ismail
Marinković, Aleksandar
Article (Published version)
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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 i...ntramolecular charge transfer character.
Keywords:
phthalides / solvatochromism / substituent effect / LSER / quantum chemical calculationSource:
Journal of the Serbian Chemical Society, 2018, 83, 2, 139-155Publisher:
- Srpsko hemijsko društvo, Beograd
Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.2298/JSC170408003P
ISSN: 0352-5139
WoS: 000428178800001
Scopus: 2-s2.0-85044276561
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Prlainović, Nevena AU - Rančić, Milica AU - Stojiljković, Ivana AU - Nikolić, Jasmina AU - Drmanić, Saša AU - Ajaj, Ismail AU - Marinković, Aleksandar PY - 2018 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3968 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 ER -
@article{ author = "Prlainović, Nevena and Rančić, Milica and Stojiljković, Ivana and Nikolić, Jasmina and Drmanić, Saša and Ajaj, Ismail and Marinković, Aleksandar", 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" }
Prlainović, N., Rančić, M., Stojiljković, I., Nikolić, J., Drmanić, S., Ajaj, I.,& Marinković, A.. (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
Prlainović N, Rančić M, Stojiljković I, Nikolić J, Drmanić S, Ajaj I, Marinković A. 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 .
Prlainović, Nevena, Rančić, Milica, Stojiljković, Ivana, Nikolić, Jasmina, Drmanić, Saša, Ajaj, Ismail, Marinković, Aleksandar, "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 . .