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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)...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2016
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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. |
format | Online Article Text |
id | pubmed-6273986 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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