European Journal of Chemistry

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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Madhu Kumar Dogganal Jayappa
Prabhuswamy Akhileshwari
Mandayam Anandalwar Sridhar
Lohith Tumakuru Nagarajappa
Shivegowda Nagaraju
Subrayachar Raghavendra
Manasa Dogganal Jayappa

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)°, = 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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Jayappa, M. K. D.; Akhileshwari, P.; Sridhar, M. A.; Nagarajappa, L. T.; Nagaraju, S.; Raghavendra, S.; Jayappa, M. D. Synthesis and Detailed Characterization of a Newly Synthesized Chalcone, 3-(2,5-Dimethoxyphenyl)-1-(naphthalen-2-yl)prop-2-En-1-One. Eur. J. Chem. 2021, 12, 69-76.

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Supporting Agencies

Department of Science and Technology - Karnataka Science and Technology Promotion Society (DST-KSTePS), Government of Karnataka, India.
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