Synthesis, crystal structure analysis, spectral IR, UV–Vis, NMR assessments, electronic and nonlinear optical properties of potent quinoline based derivatives: Interplay of experimental and DFT Study

Publication date: Available online 10 October 2018Source: Journal of Saudi Chemical SocietyAuthor(s): Muhammad Khalid, Muhammad Adeel, Malik Aman Ullah, Muhammad Usman Khan, Muhammad Nawaz Tahir, Ataualpa Albert Carmo BragaAbstractQuinoline and its derivatives are widely studied by both synthetic and computational chemists due to their exciting perspectives in biological and nonlinear optical (NLO) research. Herein, three novel arylated quinolines: 3-(4-acetylphenyl)quinoline (1), 3-(4-(methylthio)phenyl)-quinoline (2) and 3-(4-phenoxyphenyl)quinoline (3) were synthesized employing Pd catalyzed Suzuki-Miyaura cross-coupling reaction. The chemical structures of all compounds were resolved employing different analytical techniques like 1H-NMR, FT-IR, UV-Vis, EIMS, elemental analysis and finally confirmed by single crystal X-ray diffraction analysis. Synthesized compounds were further subjected to density functional theory (DFT) calculations at B3LYP level of theory in conjunction with 6-311+G(2d,p) basis set to explore optimized geometry, natural bond orbital (NBO) analysis, FT-IR spectroscopic data, frontier molecular orbitals (FMOs) and NLO properties. Overall, a good agreement was found between DFT computed results and corresponding experimental findings. Vertical electronic transition states were computationally calculated using time-dependent DFT (TDDFT) at same B3LYP level of theory and 6-311+G(2d,p) basis set combination. NBO calculations indicated the occurrence of intr...
Source: Journal of Saudi Chemical Society - Category: Chemistry Source Type: research