

Synthesis and detailed characterization of a newly synthesized chalcone, 3-(2,5-dimethoxyphenyl)-1-(naphthalen-2-yl)prop-2-en-1-one
Madhu Kumar Dogganal Jayappa (1)







(1) Faculty of Pharmacy, Ramaiah Institute of Applied Sciences, Bengaluru 560 054, India
(2) Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
(3) Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
(4) Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru 570 006, India
(5) Department of Engineering Physics, Adichunchanagiri Institute of Technology, Chikkamagaluru 577 102, India
(6) Department of Engineering Physics, Adichunchanagiri Institute of Technology, Chikkamagaluru 577 102, India
(7) Department of Applied Botany, Davanagere University, Davanagere 577 007, India
(*) Corresponding Author
Received: 12 Jan 2021 | Revised: 11 Feb 2021 | Accepted: 18 Feb 2021 | Published: 31 Mar 2021 | Issue Date: March 2021
Abstract
Chalcones are the main component of some natural compounds. The title compound, 3-(2,5-dimethoxyphenyl)-1-(naphthalen-2-yl)prop-2-en-1-one, was synthesized and characterized. The compound (C21H18O3) crystallizes in the triclinic system with the space group of P-1 (no. 2), a = 7.7705(4) Å, b = 10.2634(6) Å, c = 11.2487(6) Å, α = 79.655(5)°, β = 81.500(5)°, γ = 68.039(5)°, V = 815.28(9) Å3, Z = 2, T = 293(2) K, μ(MoKα) = 0.086 mm-1, Dcalc = 1.297 g/cm3, 9126 reflections measured (4.318° ≤ 2Θ ≤ 52.728°), 3302 unique (Rint = 0.0466, Rsigma = 0.0528) which were used in all calculations. The final R1 was 0.0568 (I > 2σ(I)) and wR2 was 0.1667 (all data). The crystal structure is stabilized by both short C-H···O inter- and intra-molecular interactions. In addition, the crystal structure is reinforced by π-π interactions. Hirshfeld surface analysis confirmed the presence of C-H···O intermolecular interactions. The two-dimensional fingerprint plots are used to visualize the individual interactions present in the molecule. DFT calculations were performed to know the energy levels of the frontier molecular orbitals (HOMO-LUMO). The energy gap between the frontier molecular orbitals shows the kinetic stability of the molecule. The chemical reactive sites are observed by generating MEP surface. Non-covalent interactions (NCIs) are analyzed using reduced density gradient (RDG) analysis.
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DOI: 10.5155/eurjchem.12.1.69-76.2067
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Department of Science and Technology - Karnataka Science and Technology Promotion Society (DST-KSTePS), Government of Karnataka, India.
Citations
[1]. P. Akhileshwari, K. R. Kiran, M. A. Sridhar, M. P. Sadashiva
Crystal Structure Characterization, Interaction Energy Analysis and DFT Studies of 3-(4-Chlorophenyl)-N-phenylquinoxalin-2-amine
Journal of Chemical Crystallography 53(2), 185, 2023
DOI: 10.1007/s10870-022-00959-9

[2]. Nesrin Mahmoud Morsy, Ashraf Sayed Hassan
Synthesis, reactions, and applications of chalcones: A review
European Journal of Chemistry 13(2), 241, 2022
DOI: 10.5155/eurjchem.13.2.241-252.2245

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