Synthesis, spectroscopic investigations (FT-IR, NMR, UV–Vis, and TD-DFT), and molecular docking of (E)-1-(benzo[d][1, 3]dioxol-6-yl)-3-(6-methoxynaphthalen-2-yl)prop-2-en-1-one

• Published in: Journal of molecular structure 2017-02, Vol.1130, p.1018-1023
• Main Authors: Therasa Alphonsa, A., Loganathan, C., Athavan Alias Anand, S., Kabilan, S.
• Format: Article
• Language: English
• Subjects: 4ZYC; DFT; MEP; Molecular docking; NBO; VEDA
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2016.10.005

The compound (E)-1-(benzo [d] [1, 3] dioxol-6-yl)-3-(6-methoxy naphthalen-2-yl) prop-2-en-1-one (AKN) was synthesized and characterized by FT-IR, NMR, and UV–Vis spectrometer. The optimized molecular geometry, bond lengths, bond angles, atomic charges, harmonic vibrational wave numbers and intensities of vibrational bonds of the title compound have been investigated by Time dependent- Density Functional Theory (TD-DFT) using a standard B3LYP method with 6–31 G (d, p) basis set available in the Gaussian 09W package. 1H and 13C NMR chemical shifts of the molecule were calculated using Gauge-independent atomic orbital method (GIAO). Experimental excitation energies of the molecules were matched with the theoretically calculated energies. The atomic charge distributions of the various atoms present in the AKN were obtained by Mulliken charge population analysis. The Molecular Electrostatic Potential (MEP) analysis reveals the sites for electrophilic attack and nucleophilic reactions in the molecule. The difference between the observed and scaled frequencies was small. The HOMO to LUMO transition implies an electron density transfer. The intramolecular contacts have been interpreted using Natural Bond Orbital (NBO) analysis. The calculation results were applied to simulate spectra of the title compound, which show excellent agreement with observed spectra. To provide information about the interactions between human cytochrome protein and the novel compound theoretically, docking studies were carried out using Schrödinger software. •AKN was synthesized and characterized by IR, 1H, 13C NMR, UV and Mass spectroscopy.•Optimized geometry, HOMO-LUMO, MEP, Polarizability, NBO and Docking were discussed.•1H and values 13C NMR chemical shifts have been compared with experimental.•Theoretical IR frequencies are analyzed by TED% using VEDA 4 program.•Computational technique were carried out by B3LYP/6-31G (d, p) basis set.