Synthesis and detailed characterization of a newly synthesized chalcone, 3-(2,5-dimethoxyphenyl)-1-(naphthalen-2-yl)prop-2-en-1-one
Open Access
- 31 March 2021
- journal article
- Published by European Journal of Chemistry in European Journal of Chemistry
- Vol. 12 (1), 69-76
- https://doi.org/10.5155/eurjchem.12.1.69-76.2067
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.Keywords
This publication has 24 references indexed in Scilit:
- Multiwfn: A multifunctional wavefunction analyzerJournal of Computational Chemistry, 2011
- Hirshfeld surface analysisCrystEngComm, 2008
- A short history of SHELXActa Crystallographica Section A Foundations of Crystallography, 2007
- Synthesis and Characterization of Some CoIIIand CrIIIComplexes Containing Diazine LigandsSynthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 2007
- CrystalExplorer: a tool for displaying Hirshfeld surfaces and visualising intermolecular interactions in molecular crystalsActa Crystallographica Section A Foundations of Crystallography, 2006
- A novel definition of a molecule in a crystalChemical Physics Letters, 1997
- VMD: Visual molecular dynamicsJournal of Molecular Graphics, 1996
- General atomic and molecular electronic structure systemJournal of Computational Chemistry, 1993
- Chalcones from Humulus lupulusPhytochemistry, 1989
- Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compoundsJournal of the Chemical Society, Perkin Transactions 2, 1987