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.
TY - JOUR
AU - Banjac, Nebojša R.
AU - Božić, Bojan
AU - Mirkovic, Jelena M.
AU - Vitnik, Vesna
AU - Vitnik, Željko
AU - Valentić, Nataša V.
AU - Ušćumlić, Gordana
PY - 2017
UR - http://cer.ihtm.bg.ac.rs/handle/123456789/2054
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
T2 - Journal of Molecular Structure
T1 - Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides
VL - 1129
SP - 271
EP - 282
DO - 10.1016/j.molstruc.2016.09.086
ER -
@article{
author = "Banjac, Nebojša R. and Božić, Bojan and Mirkovic, Jelena M. and Vitnik, Vesna and Vitnik, Željko and Valentić, Nataša V. and Ušćumlić, Gordana",
year = "2017",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/2054",
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",
journal = "Journal of Molecular Structure",
title = "Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides",
volume = "1129",
pages = "271-282",
doi = "10.1016/j.molstruc.2016.09.086"
}
Banjac, N. R., Božić, B., Mirkovic, J. M., Vitnik, V., Vitnik, Ž., Valentić, N. V.,& Ušćumlić, G. (2017). Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides.
Journal of Molecular Structure
Elsevier., 1129, 271-282.
https://doi.org/10.1016/j.molstruc.2016.09.086
Banjac NR, Božić B, Mirkovic JM, Vitnik V, Vitnik Ž, Valentić NV, Ušćumlić G. Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides. Journal of Molecular Structure. 2017;1129:271-282
Banjac Nebojša R., Božić Bojan, Mirkovic Jelena M., Vitnik Vesna, Vitnik Željko, Valentić Nataša V., Ušćumlić Gordana, "Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides" Journal of Molecular Structure, 1129 (2017):271-282,
https://doi.org/10.1016/j.molstruc.2016.09.086 .
