Synthesis and detailed characterization of a newly synthesized chalcone, 3-(2,5-dimethoxyphenyl)-1-(naphthalen-2-yl)prop-2-en-1-one
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Published:2021-03-31
Issue:1
Volume:12
Page:69-76
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ISSN:2153-2257
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Container-title:European Journal of Chemistry
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language:en
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Short-container-title:Eur J Chem
Author:
Jayappa Madhu Kumar Dogganal1ORCID, Akhileshwari Prabhuswamy2ORCID, Sridhar Mandayam Anandalwar2ORCID, Nagarajappa Lohith Tumakuru2ORCID, Nagaraju Shivegowda3ORCID, Raghavendra Subrayachar3ORCID, Jayappa Manasa Dogganal4ORCID
Affiliation:
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 Engineering Physics, Adichunchanagiri Institute of Technology, Chikkamagaluru 577 102, India 4. Department of Applied Botany, Davanagere University, Davanagere 577 007, India
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.
Publisher
European Journal of Chemistry
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