European Journal of Chemistry 2023, 14(2), 287-296 | doi: | Get rights and content

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Synthesis, computational studies, and Hirshfeld surface analysis of 2H-chromen-2-one and imine derivatives

Felix Odame (1,*) orcid , Tatenda Madanhire (2) orcid , Jerry Joe Ebo Kingsley Harrison (3) orcid , Nathaniel Owusu Boadi (4) orcid , Eric Hosten (5) orcid

(1) Department of Basic Sciences, School of Basics and Biomedical Sciences, University of Health and Allied Sciences, PMB 31, Ho, Ghana
(2) Department of Chemistry, Nelson Mandela University, PO Box 77000, Gqeberha 6000, South Africa
(3) Department of Chemistry, University of Ghana, PO Box LG 56, Legon, Accra, Ghana
(4) Department of Chemistry, Kwame Nkrumah University of Science and Technology, Kumasi, University Post Office, Kumasi, Ghana
(5) Department of Chemistry, Nelson Mandela University, PO Box 77000, Gqeberha 6000, South Africa
(*) Corresponding Author

Received: 18 Dec 2022 | Revised: 06 Mar 2023 | Accepted: 26 Mar 2023 | Published: 30 Jun 2023 | Issue Date: June 2023


Some 2H-chromen-2-one and imine derivatives have been synthesized through a one-pot condensation of aldehydes, diethyl malonate, and amine compounds. The compounds obtained have been characterized using FTIR, NMR, GC-MS, and elemental analysis. The single-crystal X-ray structure of 3-[piperidine-1-carbonyl]-2H-chromen-2-one (2) has been presented. Compound 2, recrystallized in the monoclinic space C2/c (no. 15), a = 16.654(15) Å, b = 8.789(7) Å, c = 18.460(18) Å, β = 102.89(5)°, = 2634(4) Å3, Z = 8, T = 296(2) K, μ(MoKα) = 0.091 mm-1, Dcalc = 1.298 g/cm3, 17626 reflections measured (4.528° ≤ 2Θ ≤ 57.446°), 3321 unique (Rint = 0.0313, Rsigma = 0.0257) which were used in all calculations. The final R1 was 0.0441 (I > 2σ(I)) and wR2 was 0.1329 (all data). The experimental bond lengths, bond angles, and other topological properties of compound 2 were compared with the DFT calculated results, the comparison showed good agreement with each other with varying level deviations. The energy levels of HOMO and LUMO, as well as the global chemical reactivity descriptors of representative compound 2, have been presented. A discussion of the Hirshfeld surface analysis of compound 2 has been carried out to provide insight into its structural properties.


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European Journal of Chemistry


Imine; Crystal; Coumarin; Monoclinic; Chemical reactivity; Hirshfeld surface analysis

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DOI: 10.5155/eurjchem.14.2.287-296.2389

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The authors acknowledge the Centre for High Performance Computing in South Africa for the use of their computing resources (CHEM1261).


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Odame, F.; Madanhire, T.; Harrison, J.; Boadi, N.; Hosten, E. Eur. J. Chem. 2023, 14(2), 287-296. doi:10.5155/eurjchem.14.2.287-296.2389
Odame, F.; Madanhire, T.; Harrison, J.; Boadi, N.; Hosten, E. Synthesis, computational studies, and Hirshfeld surface analysis of 2H-chromen-2-one and imine derivatives. Eur. J. Chem. 2023, 14(2), 287-296. doi:10.5155/eurjchem.14.2.287-296.2389
Odame, F., Madanhire, T., Harrison, J., Boadi, N., & Hosten, E. (2023). Synthesis, computational studies, and Hirshfeld surface analysis of 2H-chromen-2-one and imine derivatives. European Journal of Chemistry, 14(2), 287-296. doi:10.5155/eurjchem.14.2.287-296.2389
Odame, Felix, Tatenda Madanhire, Jerry Joe Ebo Kingsley Harrison, Nathaniel Owusu Boadi, & Eric Hosten. "Synthesis, computational studies, and Hirshfeld surface analysis of 2H-chromen-2-one and imine derivatives." European Journal of Chemistry [Online], 14.2 (2023): 287-296. Web. 3 Oct. 2023
Odame, Felix, Madanhire, Tatenda, Harrison, Jerry, Boadi, Nathaniel, AND Hosten, Eric. "Synthesis, computational studies, and Hirshfeld surface analysis of 2H-chromen-2-one and imine derivatives" European Journal of Chemistry [Online], Volume 14 Number 2 (30 June 2023)

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