European Journal of Chemistry 2021, 12(1), 69-76 | doi: https://doi.org/10.5155/eurjchem.12.1.69-76.2067 | Get rights and content

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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) orcid , Prabhuswamy Akhileshwari (2,*) orcid , Mandayam Anandalwar Sridhar (3) orcid , Lohith Tumakuru Nagarajappa (4) orcid , Shivegowda Nagaraju (5) orcid , Subrayachar Raghavendra (6) orcid , Manasa Dogganal Jayappa (7) orcid

(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)°, = 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.


Keywords


Chalcone; Single crystal structure; Reduced density gradient; Hirshfeld surface analysis; Frontier molecular orbitals; Molecular electrostatic potential

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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.

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Jayappa, M.; Akhileshwari, P.; Sridhar, M.; Nagarajappa, L.; Nagaraju, S.; Raghavendra, S.; Jayappa, M. Eur. J. Chem. 2021, 12(1), 69-76. doi:10.5155/eurjchem.12.1.69-76.2067
Jayappa, M.; Akhileshwari, P.; Sridhar, M.; Nagarajappa, L.; Nagaraju, S.; Raghavendra, S.; Jayappa, M. 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(1), 69-76. doi:10.5155/eurjchem.12.1.69-76.2067
Jayappa, M., Akhileshwari, P., Sridhar, M., Nagarajappa, L., Nagaraju, S., Raghavendra, S., & Jayappa, M. (2021). Synthesis and detailed characterization of a newly synthesized chalcone, 3-(2,5-dimethoxyphenyl)-1-(naphthalen-2-yl)prop-2-en-1-one. European Journal of Chemistry, 12(1), 69-76. doi:10.5155/eurjchem.12.1.69-76.2067
Jayappa, Madhu, Prabhuswamy Akhileshwari, Mandayam Anandalwar Sridhar, Lohith Tumakuru Nagarajappa, Shivegowda Nagaraju, Subrayachar Raghavendra, & Manasa Dogganal Jayappa. "Synthesis and detailed characterization of a newly synthesized chalcone, 3-(2,5-dimethoxyphenyl)-1-(naphthalen-2-yl)prop-2-en-1-one." European Journal of Chemistry [Online], 12.1 (2021): 69-76. Web. 17 Jun. 2021
Jayappa, Madhu, Akhileshwari, Prabhuswamy, Sridhar, Mandayam, Nagarajappa, Lohith, Nagaraju, Shivegowda, Raghavendra, Subrayachar, AND Jayappa, Manasa. "Synthesis and detailed characterization of a newly synthesized chalcone, 3-(2,5-dimethoxyphenyl)-1-(naphthalen-2-yl)prop-2-en-1-one" European Journal of Chemistry [Online], Volume 12 Number 1 (31 March 2021)

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