Theoretical Study of 1,3-Dipolar Cycloadditions Regioselectivity of Benzyl Azide with Glycosyl-O Acetylene Using Density Functional Theory (DFT)

Adib Ghaleb, Adnane Aouidate, Abdelouahid Sbai, Tahar Lakhlifi, Hamid Maghat, Mouhamed Bouachrine

Abstract


A theoretical study of 1,3-cycloaddition has been carried out using density functional theory (DFT) methods at the B3LYP/6-31G* level. The regioselectivity of the reaction have been clarified through different theoretical approaches: Case of a Two-Center Process (Domingo approach), HSAB principle (Gazquez and Mendez approach), and the activation energy calculations. The analysis of results shows that the reaction takes place along concerted asynchronous mechanism and the isomer meta is favored, in agreement with the experiment results.

 

DOI: http://dx.doi.org/10.17807/orbital.v9i5.1017

 


Keywords


1, 3-dipolar cycloadditions; 1,2,3-Triazole; regioselectivity; DFT calculations; fukui indices.

Full Text: PDF

Refbacks

  • There are currently no refbacks.


Creative Commons License
This work is licensed under a Creative Commons Attribution 3.0 License.

Orbital: The Electronic Journal of Chemistry (e-ISSN 1984-6428) is a quarterly scientific journal published by the Institute of Chemistry of the Universidade Federal de Mato Grosso do Sul, Brazil. Orbital is a peer-reviewed, open-access journal.