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
Joint Authors
Khalid, Muhammad
Aman Allah, Malik
Khan, Muhammad Uthman
Tahir, Muhammad Nawaz
Braga, Ataualpa Albert Carmo
Adil, Muhammad
Source
Journal of Saudi Chemical Society
Issue
Vol. 23, Issue 5 (31 Jul. 2019), pp.546-560, 15 p.
Publisher
Publication Date
2019-07-31
Country of Publication
Saudi Arabia
No. of Pages
15
Main Subjects
Topics
Abstract EN
Quinoline 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 intra-molecular charge transfer in synthesized compounds, hence enormous molecular stability owing to hyperconjugative interactions.
Energy of FMOs was used to calculate the global reactivity descriptors which indicated that synthesized molecules are chemically hard compounds with greater kinetic stability and electron donating capability.
NLO properties were found to be in the range 1830–2960 a.u and order of 2 > 1 > 3.
Urea molecule comparative analysis and two-state model confirmed that synthesized molecules are excellent NLO candidates and may have prospective uses in the technology related applications.
American Psychological Association (APA)
Khalid, Muhammad& Aman Allah, Malik& Adil, Muhammad& Khan, Muhammad Uthman& Tahir, Muhammad Nawaz& Braga, Ataualpa Albert Carmo. 2019. 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. Journal of Saudi Chemical Society،Vol. 23, no. 5, pp.546-560.
https://search.emarefa.net/detail/BIM-889256
Modern Language Association (MLA)
Khalid, Muhammad…[et al.]. 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. Journal of Saudi Chemical Society Vol. 23, no. 5 (Jul. 2019), pp.546-560.
https://search.emarefa.net/detail/BIM-889256
American Medical Association (AMA)
Khalid, Muhammad& Aman Allah, Malik& Adil, Muhammad& Khan, Muhammad Uthman& Tahir, Muhammad Nawaz& Braga, Ataualpa Albert Carmo. 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. Journal of Saudi Chemical Society. 2019. Vol. 23, no. 5, pp.546-560.
https://search.emarefa.net/detail/BIM-889256
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references : p. 559-560
Record ID
BIM-889256