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

The relationship between the electrophilicity ω index and the Hammett constant σ(p) 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)...

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Autores principales: Ben El Ayouchia, Hicham, Anane, Hafid, El Idrissi Moubtassim, Moulay Lahcen, Domingo, Luis R., Julve, Miguel, Stiriba, Salah-Eddine
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273986/
https://www.ncbi.nlm.nih.gov/pubmed/27801811
http://dx.doi.org/10.3390/molecules21111434
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author Ben El Ayouchia, Hicham
Anane, Hafid
El Idrissi Moubtassim, Moulay Lahcen
Domingo, Luis R.
Julve, Miguel
Stiriba, Salah-Eddine
author_facet Ben El Ayouchia, Hicham
Anane, Hafid
El Idrissi Moubtassim, Moulay Lahcen
Domingo, Luis R.
Julve, Miguel
Stiriba, Salah-Eddine
author_sort Ben El Ayouchia, Hicham
collection PubMed
description The relationship between the electrophilicity ω index and the Hammett constant σ(p) 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 σ(p). 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.
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spelling pubmed-62739862018-12-28 A Theoretical Study of the Relationship between the Electrophilicity ω Index and Hammett Constant σ(p) in [3+2] Cycloaddition Reactions of Aryl Azide/Alkyne Derivatives Ben El Ayouchia, Hicham Anane, Hafid El Idrissi Moubtassim, Moulay Lahcen Domingo, Luis R. Julve, Miguel Stiriba, Salah-Eddine Molecules Article The relationship between the electrophilicity ω index and the Hammett constant σ(p) 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 σ(p). 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. MDPI 2016-10-27 /pmc/articles/PMC6273986/ /pubmed/27801811 http://dx.doi.org/10.3390/molecules21111434 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Ben El Ayouchia, Hicham
Anane, Hafid
El Idrissi Moubtassim, Moulay Lahcen
Domingo, Luis R.
Julve, Miguel
Stiriba, Salah-Eddine
A Theoretical Study of the Relationship between the Electrophilicity ω Index and Hammett Constant σ(p) in [3+2] Cycloaddition Reactions of Aryl Azide/Alkyne Derivatives
title A Theoretical Study of the Relationship between the Electrophilicity ω Index and Hammett Constant σ(p) in [3+2] Cycloaddition Reactions of Aryl Azide/Alkyne Derivatives
title_full A Theoretical Study of the Relationship between the Electrophilicity ω Index and Hammett Constant σ(p) in [3+2] Cycloaddition Reactions of Aryl Azide/Alkyne Derivatives
title_fullStr A Theoretical Study of the Relationship between the Electrophilicity ω Index and Hammett Constant σ(p) in [3+2] Cycloaddition Reactions of Aryl Azide/Alkyne Derivatives
title_full_unstemmed A Theoretical Study of the Relationship between the Electrophilicity ω Index and Hammett Constant σ(p) in [3+2] Cycloaddition Reactions of Aryl Azide/Alkyne Derivatives
title_short A Theoretical Study of the Relationship between the Electrophilicity ω Index and Hammett Constant σ(p) in [3+2] Cycloaddition Reactions of Aryl Azide/Alkyne Derivatives
title_sort theoretical study of the relationship between the electrophilicity ω index and hammett constant σ(p) in [3+2] cycloaddition reactions of aryl azide/alkyne derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273986/
https://www.ncbi.nlm.nih.gov/pubmed/27801811
http://dx.doi.org/10.3390/molecules21111434
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