Molecular docking, expounding the regiospecificity, stereoselectivity, and the mechanism of [5+2] cycloaddition reaction between ethereal ether and oxidopyrylium

Application of molecular electron density theory (MEDT) to investigate the [5+2] cycloaddition reaction between oxidopyrylium and ethervinylether, we discovered that oxidopyrylium is an electrophile and ethervinylether is a nucleophile by an examination of conceptual DFT indices. Analysis of energet...

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Published in:Structural chemistry 2024-06, Vol.35 (3), p.841-852
Main Authors: Aitouna, Anas Ouled, Mazoir, Noureddine, Zeroual, Abdellah, Syed, Asad, Bahkali, Ali H., Elgorban, Abdallah M., Verma, Meenakshi, idrissi, Mohammed El, Jasiński, Radomir
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Computer Applications in Chemistry
Cycloaddition
Electron density
Molecular docking
Nucleophiles
Physical Chemistry
Stereoselectivity
Theoretical and Computational Chemistry
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Summary:Application of molecular electron density theory (MEDT) to investigate the [5+2] cycloaddition reaction between oxidopyrylium and ethervinylether, we discovered that oxidopyrylium is an electrophile and ethervinylether is a nucleophile by an examination of conceptual DFT indices. Analysis of energetical parameters shows clearly that this cycloaddition is both regio- and stereoselective, which is extremely consistent with the experience. Topological analysis of the electron localization function (ELF) has shown that this [5+2] cycloaddition is achieved by a two-step, single-step mechanism along the most favored route. Aside from that, docking outcomes show that the ( 1 – 20 ) oxabicyclo[3.2.1]octene derivatives have a significant anti-HIV potential.
ISSN:1040-0400
1572-9001
DOI:10.1007/s11224-023-02239-4