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Vol. 35 No. 8 (2023): Vol 35 Issue 8, 2023

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Synthesis and DFT Study of 7-Bromophenylnaphthopyran Moieties

https://doi.org/10.14233/ajchem.2023.28032
Ashraf Hassan Fekry Abd El-Wahab
Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Saudi Arabia
https://orcid.org/0000-0001-5205-8026
Hany Mostafa Mohamed
Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Saudi Arabia
https://orcid.org/0000-0002-9575-5435

Corresponding Author(s) : Ashraf Hassan Fekry Abd El-Wahab

ahabdelwahab@jazanu.edu.sa

Asian Journal of Chemistry, Vol. 35 No. 8 (2023): Vol 35 Issue 8, 2023

Abstract

A one-pot, three-component reaction of 6-bromo-2-naphthol (1), p-chlorobenzaldehyde (2) and malononitrile or ethyl cyanoacetate (3) in ethanol/piperidine under reflux was performed to afford 4H-naphtho[2,1-b]pyrano-3-carbonitrile (4a) and ethyl 4H-naphtho[2,1-b]pyrano-3-carboxylate (4b) derivatives, respectively. The structure of these compounds was determined using IR, 1H NMR, 13C NMR, mass spectroscopy and UV-Vis spectra. The molecular geometry of compounds 4a and 4b was determined at the B3LYP/631+G(d) level. The geometric optimization was performed on two tautomers and two conformers. Tautomers were separated by about 7.942 kcal/mol, while rotational conformers were separated by just 0.511 kcal/mol. The global electrophilicity, hardness, softness and local condensed Fukui functions were calculated and considered as molecular reactivity descriptors, moreover the frontier molecular orbitals (HOMO and LUMO) were also calculated.

Keywords

6-Bromo-2-naphthol 4-Chlorobenzaldehyde Malononitrile Ethyl cyanoacetate Fukui functions Density functional theory
El-Wahab, A. H. F. A., & Mohamed, H. M. (2023). Synthesis and DFT Study of 7-Bromophenylnaphthopyran Moieties. Asian Journal of Chemistry, 35(8), 1819–1826. https://doi.org/10.14233/ajchem.2023.28032
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