Detailed solvent, structural, quantum chemical study and antimicrobial activity of isatin Schiff base
Authors
Brkić, Dominik R.Božić, Aleksandra R.
Marinković, Aleksandar
Milčić, Miloš K.
Prlainović, Nevena Z.
Assaleh, Fathi H.
Cvijetić, Ilija
Nikolić, Jasmina B.
Drmanić, Saga Z.
Article (Accepted Version)
Metadata
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The ratios of E/Z isomers of sixteen synthesized 1,3-dihydro-3-(substituted phenylimino)-2H-indol-2-one were studied using experimental and theoretical methodology. Linear solvation energy relationships (LSER) rationalized solvent influence of the solvent-solute interactions on the UV-Vis absorption maxima shifts (v(max)) of both geometrical isomers using the Kamlet-Taft equation. Linear free energy relationships (LEER) in the form of single substituent parameter equation (SSP) was used to analyze substituent effect on pK(a), NMR chemical shifts and v(max) values. Electron charge density was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Bader's analysis. The substituent and solvent effect on intramolecular charge transfer (ICT) were interpreted with the aid of time-dependent density functional (TD-DFT) method. Additionally, the results of TD-DFT calculations quantified the efficiency of ICT from the calculated charge-transfer distance (D-CT) and amount of transferre...d charge (Q(CT)). The antimicrobial activity was evaluated using broth microdilution method. 3D QSAR modeling was used to demonstrate the influence of substituents effect as well as molecule geometry on antimicrobial activity. (C) 2018 Elsevier B.V. All rights reserved.
Keywords:
E/Z isomers / Solvent effects / Substituent effects / Bader's analysis / TD-DFT, 3D QSARSource:
Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 2018, 196, 16-30Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-MESTD-Basic Research (BR or ON)-172013)
Note:
- This is peer-reviewed version of the following article: Brkić, D. R.; Božić, A. R.; Marinković, A. D.; Milčić, M. K.; Prlainović, N. Ž.; Assaleh, F. H.; Cvijetić, I. N.; Nikolić, J. B.; Drmanić, S. Ž. Detailed Solvent, Structural, Quantum Chemical Study and Antimicrobial Activity of Isatin Schiff Base. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy 2018, 196, 16–30. https://doi.org/10.1016/j.saa.2018.01.080
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3197
DOI: 10.1016/j.saa.2018.01.080
ISSN: 1386-1425
PubMed: 29428893
WoS: 000428833000003
Scopus: 2-s2.0-85041496731
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Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Brkić, Dominik R. AU - Božić, Aleksandra R. AU - Marinković, Aleksandar AU - Milčić, Miloš K. AU - Prlainović, Nevena Z. AU - Assaleh, Fathi H. AU - Cvijetić, Ilija AU - Nikolić, Jasmina B. AU - Drmanić, Saga Z. PY - 2018 UR - https://cherry.chem.bg.ac.rs/handle/123456789/3196 AB - The ratios of E/Z isomers of sixteen synthesized 1,3-dihydro-3-(substituted phenylimino)-2H-indol-2-one were studied using experimental and theoretical methodology. Linear solvation energy relationships (LSER) rationalized solvent influence of the solvent-solute interactions on the UV-Vis absorption maxima shifts (v(max)) of both geometrical isomers using the Kamlet-Taft equation. Linear free energy relationships (LEER) in the form of single substituent parameter equation (SSP) was used to analyze substituent effect on pK(a), NMR chemical shifts and v(max) values. Electron charge density was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Bader's analysis. The substituent and solvent effect on intramolecular charge transfer (ICT) were interpreted with the aid of time-dependent density functional (TD-DFT) method. Additionally, the results of TD-DFT calculations quantified the efficiency of ICT from the calculated charge-transfer distance (D-CT) and amount of transferred charge (Q(CT)). The antimicrobial activity was evaluated using broth microdilution method. 3D QSAR modeling was used to demonstrate the influence of substituents effect as well as molecule geometry on antimicrobial activity. (C) 2018 Elsevier B.V. All rights reserved. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy T1 - Detailed solvent, structural, quantum chemical study and antimicrobial activity of isatin Schiff base VL - 196 SP - 16 EP - 30 DO - 10.1016/j.saa.2018.01.080 ER -
@article{ author = "Brkić, Dominik R. and Božić, Aleksandra R. and Marinković, Aleksandar and Milčić, Miloš K. and Prlainović, Nevena Z. and Assaleh, Fathi H. and Cvijetić, Ilija and Nikolić, Jasmina B. and Drmanić, Saga Z.", year = "2018", abstract = "The ratios of E/Z isomers of sixteen synthesized 1,3-dihydro-3-(substituted phenylimino)-2H-indol-2-one were studied using experimental and theoretical methodology. Linear solvation energy relationships (LSER) rationalized solvent influence of the solvent-solute interactions on the UV-Vis absorption maxima shifts (v(max)) of both geometrical isomers using the Kamlet-Taft equation. Linear free energy relationships (LEER) in the form of single substituent parameter equation (SSP) was used to analyze substituent effect on pK(a), NMR chemical shifts and v(max) values. Electron charge density was obtained by the use of Quantum Theory of Atoms in Molecules, i.e. Bader's analysis. The substituent and solvent effect on intramolecular charge transfer (ICT) were interpreted with the aid of time-dependent density functional (TD-DFT) method. Additionally, the results of TD-DFT calculations quantified the efficiency of ICT from the calculated charge-transfer distance (D-CT) and amount of transferred charge (Q(CT)). The antimicrobial activity was evaluated using broth microdilution method. 3D QSAR modeling was used to demonstrate the influence of substituents effect as well as molecule geometry on antimicrobial activity. (C) 2018 Elsevier B.V. All rights reserved.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy", title = "Detailed solvent, structural, quantum chemical study and antimicrobial activity of isatin Schiff base", volume = "196", pages = "16-30", doi = "10.1016/j.saa.2018.01.080" }
Brkić, D. R., Božić, A. R., Marinković, A., Milčić, M. K., Prlainović, N. Z., Assaleh, F. H., Cvijetić, I., Nikolić, J. B.,& Drmanić, S. Z.. (2018). Detailed solvent, structural, quantum chemical study and antimicrobial activity of isatin Schiff base. in Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy Pergamon-Elsevier Science Ltd, Oxford., 196, 16-30. https://doi.org/10.1016/j.saa.2018.01.080
Brkić DR, Božić AR, Marinković A, Milčić MK, Prlainović NZ, Assaleh FH, Cvijetić I, Nikolić JB, Drmanić SZ. Detailed solvent, structural, quantum chemical study and antimicrobial activity of isatin Schiff base. in Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy. 2018;196:16-30. doi:10.1016/j.saa.2018.01.080 .
Brkić, Dominik R., Božić, Aleksandra R., Marinković, Aleksandar, Milčić, Miloš K., Prlainović, Nevena Z., Assaleh, Fathi H., Cvijetić, Ilija, Nikolić, Jasmina B., Drmanić, Saga Z., "Detailed solvent, structural, quantum chemical study and antimicrobial activity of isatin Schiff base" in Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 196 (2018):16-30, https://doi.org/10.1016/j.saa.2018.01.080 . .