Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides
AuthorsBanjac, Nebojša R.
Mirkovic, Jelena M.
Valentić, Nataša V.
Article (Accepted Version)
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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 calculation
Source:Journal of Molecular Structure, 2017, 1129, 271-282
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
- Modeling and Numerical Simulations of Complex Many-Body Systems (RS-171017)
- This is peer-reviewed version of the article: N.R. Banjac, B.E. Božić, J.M. Mirković, V.D. Vitnik, E.J. Vitnik, N.V. Valentić, G.S. Ušćumlić, Experimental and theoretical study on the structure-property relationship of novel 1- aryl-3-methylsuccinimides, Journal of Molecular Structure, 2017, 1129, 271-282 https://dx.doi.org/10.1016/j.molstruc.2016.09.086