Detailed solvent, structural, quantum chemical study and antimicrobial activity of isatin Schiff base
2018
Authors
Brkić, Dominik R.Božić, Aleksandra R.
Marinković, Aleksandar
Milčić, Miloš
Prlainović, Nevena
Assaleh, Fathi H.
Cvijetić, Ilija
Nikolić, Jasmina
Drmanić, Saša
Article (Published version)
Metadata
Show full item recordAbstract
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.
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)
DOI: 10.1016/j.saa.2018.01.080
ISSN: 1386-1425
PubMed: 29428893
WoS: 000428833000003
Scopus: 2-s2.0-85041496731
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Brkić, Dominik R. AU - Božić, Aleksandra R. AU - Marinković, Aleksandar AU - Milčić, Miloš AU - Prlainović, Nevena AU - Assaleh, Fathi H. AU - Cvijetić, Ilija AU - Nikolić, Jasmina AU - Drmanić, Saša PY - 2018 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3971 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. 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 EP - 30 SP - 16 VL - 196 DO - 10.1016/j.saa.2018.01.080 ER -
@article{ author = "Brkić, Dominik R. and Božić, Aleksandra R. and Marinković, Aleksandar and Milčić, Miloš and Prlainović, Nevena and Assaleh, Fathi H. and Cvijetić, Ilija and Nikolić, Jasmina and Drmanić, Saša", 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.", 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", pages = "30-16", volume = "196", doi = "10.1016/j.saa.2018.01.080" }
Brkić, D. R., Božić, A. R., Marinković, A., Milčić, M., Prlainović, N., Assaleh, F. H., Cvijetić, I., Nikolić, J.,& Drmanić, S.. (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 M, Prlainović N, Assaleh FH, Cvijetić I, Nikolić J, Drmanić S. 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, Prlainović, Nevena, Assaleh, Fathi H., Cvijetić, Ilija, Nikolić, Jasmina, Drmanić, Saša, "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 . .