A quantum mechanistic investigation into the unusual reactions of nitrilimine and nitrile oxide with 2,3,4,5-tetraphenylcyclopentadienone.

Benjamin G Akonor, Albert Aniagyei, Caroline R Kwawu, Gabriel Amankwah, Elliot S Menkah, Evans Adei

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Article in Journal of molecular modeling, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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1 citing paper in PubMed.

Computational exploration of the (3 + 2) cycloaddition reactions of 3,5-bis-(arylidene)-1-methylpiperidine-4-one with C-substituted-N-phenyl nitrones for the formation of isoxazolidine derivatives.Journal of molecular modeling · 2025
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6 authors.

Benjamin G AkonorTheoretical and Computational Chemistry Laboratory, Department of Chemistry, Kwame Nkrumah University of Science and Technology, Kumasi, Ghana.

Albert AniagyeiDepartment of Basic Sciences, University of Health and Allied Sciences, Ho, Ghana. aaniagyei@uhas.edu.gh.

Caroline R KwawuTheoretical and Computational Chemistry Laboratory, Department of Chemistry, Kwame Nkrumah University of Science and Technology, Kumasi, Ghana.

Gabriel AmankwahTheoretical and Computational Chemistry Laboratory, Department of Chemistry, Kwame Nkrumah University of Science and Technology, Kumasi, Ghana.

Elliot S MenkahTheoretical and Computational Chemistry Laboratory, Department of Chemistry, Kwame Nkrumah University of Science and Technology, Kumasi, Ghana.

Evans AdeiTheoretical and Computational Chemistry Laboratory, Department of Chemistry, Kwame Nkrumah University of Science and Technology, Kumasi, Ghana.

Funding

National Council for Tertiary Education, Ghana TALIF/KNUST/3/0008/2005

6 · The paper itself

Abstract

contextThe theoretical study investigates the [3 + 2] cycloaddition (32CA) reactions between C, N-diphenyl nitrilimine with 2,3,4,5-tetraphenylcyclopentadienone and benzonitrile oxide with 2,3,4,5-tetraphenylcyclopentadienone. Nitrilimines and nitrile oxides are dipoles used in the synthesis of several heterocyclic compounds, including spiropyrazoline oxindoles and isoxazolines. The derivatives of these compounds are found with different biological activities, such as ion channel blockers, anti-inflammatory and anticancer agents as well as antimalarial. Conceptual density functional theory (CDFT) analysis, along with the activation energies of the 32CA reaction between C, N-diphenyl nitrilimine with 2,3,4,5-tetraphenylcyclopentadienone, demonstrates concordance with the empirical findings. The 32CA reaction is found to proceed through a very polar single-step asynchronous mechanism. While deductions from the activation energies of the 32CA reaction between benzonitrile oxide and 2,3,4,5-tetraphenylcyclopentadienone are found to lead to the experimental product, the parr function analysis could not explain the observed chemo- and regioselectivity. This 32CA reaction is also found to proceed through a one-step asynchronous mechanism, though with a non-polar character. The modulation of substituents positioned at the reactive sites of the reactants is found to influence the kinetics, thermodynamics, and CDFT parameters of the two 32CA reactions, consequently impacting the observed selectivities.

methodsThe 32CA reactions between C, N-diphenyl nitrilimine with 2,3,4,5-tetraphenylcyclopentadienone and benzonitrile oxide with 2,3,4,5-tetraphenylcyclopentadienone have been explored theoretically using the density functional theory method at the hybrid ωB97X-D coupled with the split valence triple-ξ (TZ) basis set as implemented in the Gaussian 09. Solvent effects were taken into account by full optimization of the gas phase geometries through the polarizable continuum model developed within the self-consistent reaction field.

Indexed as

[3 + 2] CycloadditionNitrile oxideNitriliminesSelectivitySpirocyclic

Identifiers

PMID39048781

DOI10.1007/s00894-024-06074-0

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