Synthesis and structural analysis of novel indole derivatives by XRD, spectroscopic and DFT studies

Author(s)

Tariq, Sobia ^[1] ; Raza, Abdul Rauf ^[1] ; Khalid, Muhammad ^[2] ; Rubab, Syeda Laila ^[3] ; Khan, Muhammad Usman ^[4] ; Ali, Akbar ^[1] ; Tahir, Muhammad Nawaz ^[5] ; Braga, Ataualpa Albert Carmo ^[6]

Affiliation

^[1] Univ Sargodha, Dept Chem, Ibn E Sina Block, Sargodha 40100 - Pakistan

^[2] Khwaja Fareed Univ Engn & Informat Technol, Dept Chem, Rahim Yar Khan 64200 - Pakistan

^[3] Univ Educ, Div Sci & Technol, Dept Chem, Lahore - Pakistan

^[4] Govt Coll Univ, Dept Appl Chem, Faisalabad 38000 - Pakistan

^[5] Univ Sargodha, Dept Phys, Ibn ul Hathim Block, Sargodha 40100 - Pakistan

^[6] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Ave Prof Lineu Prestes 748, BR-05508000 Sao Paulo, SP - Brazil

• Document type: Journal article
• Source: Journal of Molecular Structure; v. 1203, MAR 5 2020.
• Web of Science Citations: 9

Abstract

The indole derivatives have been getting immense interest to possess diverse applications in different fields. In present investigation, four novel indole based derivatives namely; 4,6-dimethoxy-2,3-diphenyl-1H-indole 3a, 4,5,6-trimethoxy-2,3-diphenyl-1H-indole-7-carbaldehyde 4b, N-(3'''-chlorophenyl) (4,6-dimethoxy-2,3-diphenyl-1H-indol-7-yl)methanimine 6a and N-(3'''-chlorophenyl) (4,5,6-trimethoxy-2,3-diphenyl-1H-indol-7-yl)methanimine 6b were synthesized and characterized by H-1 NMR \& C-13 NMR to resolve their molecules structures. To provide additional spectroscopic support, FT-IR and UV-Visible techniques were executed for characterization of entitle synthesized molecules. The X-ray diffraction (XRD) studies have been performed to evaluate bond angles, bond lengths, unit cells and specific space groups. Ancillary, density functional theory (DFT) study at B3LYP level of theory and 6-311 + G(d,p) basis set to investigate the optimized geometry, FT-IR vibrational analysis, frontier molecular orbital (FMO), molecular electrostatic potential (MEP) and nonlinear optical (NLO investigations. The results of single crystal studies and experimental spectroscopic studies were compared with computational insights and found in good agreement. Global reactivity parameters were estimated using energy values of FMOs. The UV-Vis spectral analysis was executed by time dependent DFT (TDDFT) at B3LYP/6-311 + G(d,p) level of theory. Two-state model and urea molecule comparative analysis evident that 3a, 4b, 6a and 6b comprise of fine NLO properties. We hope that this synergistic experimental-computational study may provide new ways for the utilization of investigated molecules for NLO associated hi-tech applications. (C) 2019 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 15/01491-3 - Theoretical study of cross-coupling reactions: homogeneous and heterogeneous catalysis
• Grantee: Ataualpa Albert Carmo Braga
• Support type: Regular Research Grants
• FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
• Grantee: Carlos Roque Duarte Correia
• Support type: Research Projects - Thematic Grants
• FAPESP's process: 11/07895-8 - Theoretical study of the Heck-Matsuda reactions
• Grantee: Ataualpa Albert Carmo Braga
• Support type: Scholarships in Brazil - Post-Doctorate