Investigation of anti-Tumor (E)-3-X-oxindole via functionalization of C20 nano structure: A DFT approach

[Display omitted] •Lack of the repulsion at exo TS held responsible for stereo-selectivity of cycloaddition.•The π aromatic stacking has significant destabilizing effect on the endo TS. In this work, cycloaddition of C20 fullerene with the selected oxindoles including (E)-3-X-oxindoles are investiga...

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Published in:Computational and theoretical chemistry 2022-08, Vol.1214, p.113763, Article 113763
Main Authors: Reza Poor Heravi, Mohammad, Mohammadi-Aghdam, Sarvin, Habibzadeh, Sepideh, Ghaffar Ebadi, Abdol, Mohammad Shoaei, Seyed, Kadhim, Mustafa M., Azizi, Bayan
Format: Article
Language:English
Subjects:
Cycloaddition
Fullerene
Oxindole
Solvent
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Summary:[Display omitted] •Lack of the repulsion at exo TS held responsible for stereo-selectivity of cycloaddition.•The π aromatic stacking has significant destabilizing effect on the endo TS. In this work, cycloaddition of C20 fullerene with the selected oxindoles including (E)-3-X-oxindoles are investigated at the density functional theory (DFT). We have operated the gas phase (g), benzene (b) 1,2-dichloroethane (d), ethanol (e), nitromethane (n), dimethyl sulfoxide (d΄) and H2O (w). The trend of dipole moment (µ) of products (Ia-IVa) also the trend of liquid phase-gas phase energy gap (ΔEl-g) seems proportional to the dielectric constant of solvent (ε). The stability of Ia-IVa seems proportional to ε and the H—bonding formation in different media. Unstable C20 similar to stable C60, with our scrutinized linear dienes can be carried out thermally exo cycloaddition at room temperature and currently hold responsible for the origin of synergistic and stereoselective, giving only one product.
ISSN:2210-271X
DOI:10.1016/j.comptc.2022.113763