Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides
2017
Authors
Banjac, NebojšaBožić, Bojan
Lađarević, Jelena
Vitnik, Vesna
Vitnik, Željko
Valentić, Nataša
Ušćumlić, Gordana
Article (Published version)
Metadata
Show full item recordAbstract
A series of ten 1-aryl-3-methylsuccinimides was synthesized and their solvatochromic properties were studied in a set of fifteen binary solvent mixtures. The solute-solvent interactions were analyzed on the basis of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The electronic effect of the substituents on the UV-Vis absorption and NMR spectra was analyzed using the simple Hammett equation. Moreover, the B3LYP, CAM-B3LYP, and M06-2X functionals using the 6-311G(d,p) basic set have been assessed in light of the position of experimental absorption maxima obtained for these compounds. The integration grid effects have also been evaluated. An interpretation of the substituent-effect transmission through the molecular skeleton and the nature of the HOMO and LUMO orbitals based on quantum-chemical calculations is given. The values of partial atomic charges from the atomic polar tenzors (APT), natural population analysis (NBO), and charges fit to the elec...trostatic potential using the B3LYP, CAM-B3LYP, and M06-2X methods are produced and correlated with different experimental properties. In order to estimate the chemical activity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of 1-phenyl-3-methylsuccinimide.
Keywords:
Succinimide / Absorption spectra / Solvent effect / Substituent effect / Quantum chemical calculationSource:
Journal of Molecular Structure, 2017, 1129, 271-282Publisher:
- Elsevier Science Bv, Amsterdam
Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-MESTD-Basic Research (BR or ON)-172013)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-MESTD-Basic Research (BR or ON)-172035)
- Modeling and Numerical Simulations of Complex Many-Body Systems (RS-MESTD-Basic Research (BR or ON)-171017)
DOI: 10.1016/j.molstruc.2016.09.086
ISSN: 0022-2860
WoS: 000389785400034
Scopus: 2-s2.0-84989911431
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Banjac, Nebojša AU - Božić, Bojan AU - Lađarević, Jelena AU - Vitnik, Vesna AU - Vitnik, Željko AU - Valentić, Nataša AU - Ušćumlić, Gordana PY - 2017 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3663 AB - A series of ten 1-aryl-3-methylsuccinimides was synthesized and their solvatochromic properties were studied in a set of fifteen binary solvent mixtures. The solute-solvent interactions were analyzed on the basis of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The electronic effect of the substituents on the UV-Vis absorption and NMR spectra was analyzed using the simple Hammett equation. Moreover, the B3LYP, CAM-B3LYP, and M06-2X functionals using the 6-311G(d,p) basic set have been assessed in light of the position of experimental absorption maxima obtained for these compounds. The integration grid effects have also been evaluated. An interpretation of the substituent-effect transmission through the molecular skeleton and the nature of the HOMO and LUMO orbitals based on quantum-chemical calculations is given. The values of partial atomic charges from the atomic polar tenzors (APT), natural population analysis (NBO), and charges fit to the electrostatic potential using the B3LYP, CAM-B3LYP, and M06-2X methods are produced and correlated with different experimental properties. In order to estimate the chemical activity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of 1-phenyl-3-methylsuccinimide. PB - Elsevier Science Bv, Amsterdam T2 - Journal of Molecular Structure T1 - Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides EP - 282 SP - 271 VL - 1129 DO - 10.1016/j.molstruc.2016.09.086 ER -
@article{ author = "Banjac, Nebojša and Božić, Bojan and Lađarević, Jelena and Vitnik, Vesna and Vitnik, Željko and Valentić, Nataša and Ušćumlić, Gordana", year = "2017", abstract = "A series of ten 1-aryl-3-methylsuccinimides was synthesized and their solvatochromic properties were studied in a set of fifteen binary solvent mixtures. The solute-solvent interactions were analyzed on the basis of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The electronic effect of the substituents on the UV-Vis absorption and NMR spectra was analyzed using the simple Hammett equation. Moreover, the B3LYP, CAM-B3LYP, and M06-2X functionals using the 6-311G(d,p) basic set have been assessed in light of the position of experimental absorption maxima obtained for these compounds. The integration grid effects have also been evaluated. An interpretation of the substituent-effect transmission through the molecular skeleton and the nature of the HOMO and LUMO orbitals based on quantum-chemical calculations is given. The values of partial atomic charges from the atomic polar tenzors (APT), natural population analysis (NBO), and charges fit to the electrostatic potential using the B3LYP, CAM-B3LYP, and M06-2X methods are produced and correlated with different experimental properties. In order to estimate the chemical activity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of 1-phenyl-3-methylsuccinimide.", publisher = "Elsevier Science Bv, Amsterdam", journal = "Journal of Molecular Structure", title = "Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides", pages = "282-271", volume = "1129", doi = "10.1016/j.molstruc.2016.09.086" }
Banjac, N., Božić, B., Lađarević, J., Vitnik, V., Vitnik, Ž., Valentić, N.,& Ušćumlić, G.. (2017). Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides. in Journal of Molecular Structure Elsevier Science Bv, Amsterdam., 1129, 271-282. https://doi.org/10.1016/j.molstruc.2016.09.086
Banjac N, Božić B, Lađarević J, Vitnik V, Vitnik Ž, Valentić N, Ušćumlić G. Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides. in Journal of Molecular Structure. 2017;1129:271-282. doi:10.1016/j.molstruc.2016.09.086 .
Banjac, Nebojša, Božić, Bojan, Lađarević, Jelena, Vitnik, Vesna, Vitnik, Željko, Valentić, Nataša, Ušćumlić, Gordana, "Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides" in Journal of Molecular Structure, 1129 (2017):271-282, https://doi.org/10.1016/j.molstruc.2016.09.086 . .