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RESEARCH PRODUCT

A Theoretical Study of the Relationship between the Electrophilicity ω Index and Hammett Constant σp in [3+2] Cycloaddition Reactions of Aryl Azide/Alkyne Derivatives

Hicham Ben El AyouchiaMoulay Lahcen El Idrissi MoubtassimSalah-eddine StiribaLuis R. DomingoMiguel JulveHafid Anane

subject

AzidesSubstituentPharmaceutical ScienceAlkynearylazides010402 general chemistryPhotochemistry01 natural sciencesArticleAnalytical Chemistrylcsh:QD241-441electrophilicity indexchemistry.chemical_compound[2+3] cycloaddition reactionslcsh:Organic chemistryComputational chemistryDrug DiscoveryReactivity (chemistry)Physical and Theoretical Chemistrychemistry.chemical_classificationsubstituent effects010405 organic chemistryArylOrganic Chemistry[2+3] cycloaddition reactions; arylazides; arylalkynes; substituent effects; electrophilicity index; Hammett constantsCycloaddition0104 chemical sciencesModels ChemicalchemistryChemistry (miscellaneous)AlkynesElectrophilearylalkynesHammett constantsMolecular MedicineDensity functional theoryAzide

description

The relationship between the electrophilicity ω index and the Hammett constant σp has been studied for the [2+3] cycloaddition reactions of a series of para-substituted phenyl azides towards para-substituted phenyl alkynes. The electrophilicity ω index—a reactivity density functional theory (DFT) descriptor evaluated at the ground state of the molecules—shows a good linear relationship with the Hammett substituent constants σp. The theoretical scale of reactivity correctly explains the electrophilic activation/deactivation effects promoted by electron-withdrawing and electron-releasing substituents in both azide and alkyne components.

yearjournalcountryeditionlanguage
2016-10-27Molecules; Volume 21; Issue 11; Pages: 1434
10.3390/molecules21111434https://dx.doi.org/10.3390/molecules21111434