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

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 (G...

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Autores: Ghaleb, Adib, Aouidate, Adnane, Sbai, Abdelouahid, Lakhlifi, Tahar, Maghat, Hamid, Bouachrine, Mohammed
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2017
País:Brasil
Institución:Universidade Federal de Mato Grosso do Sul (UFMS)
Repositorio:Orbital - The Electronic Journal of Chemistry (Campo Grande)
Idioma:inglés
OAI Identifier:oai:periodicos.ufms.br:article/16411
Acceso en línea:https://periodicos.ufms.br/index.php/orbital/article/view/16411
Access Level:acceso abierto
Palabra clave:1,3-dipolar cycloadditions
1,2,3-triazole; regioselectivity
DFT calculations
Parr functions
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spelling Theoretical Study of 1,3-Dipolar Cycloadditions Regioselectivity of Benzyl Azide with Glycosyl-O Acetylene Using Density Functional Theory (DFT)1,3-dipolar cycloadditions1,2,3-triazole; regioselectivityDFT calculationsParr functionsA 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.v9i5.1017Instituto de Química, Universidade Federal de Mato Grosso do Sul2017-12-29info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionPeer-reviewed Articleapplication/pdfhttps://periodicos.ufms.br/index.php/orbital/article/view/16411Orbital: The Electronic Journal of Chemistry; Orbital - Vol. 9 No. 5 - October - December 2017; 337-343Orbital: The Electronic Journal of Chemistry; Orbital - Vol. 9 No. 5 - October - December 2017; 337-3431984-6428reponame:Orbital - The Electronic Journal of Chemistry (Campo Grande)instname:Universidade Federal de Mato Grosso do Sul (UFMS)instacron:UFMSenghttps://periodicos.ufms.br/index.php/orbital/article/view/16411/11126Copyright (c) 2017 Orbital: The Electronic Journal of Chemistryhttps://creativecommons.org/licenses/by-nc-nd/4.0info:eu-repo/semantics/openAccessGhaleb, AdibAouidate, AdnaneSbai, AbdelouahidLakhlifi, TaharMaghat, HamidBouachrine, Mohammed2023-01-20T10:57:26Zoai:periodicos.ufms.br:article/16411Revistahttps://periodicos.ufms.br/index.php/orbital/indexPUBhttps://periodicos.ufms.br/index.php/orbital/oaieditor.orbital@ufms.br || marcos.amaral@ufms.br1984-64281984-6428opendoar:2023-01-20T10:57:26Orbital - The Electronic Journal of Chemistry (Campo Grande) - Universidade Federal de Mato Grosso do Sul (UFMS)false
dc.title.none.fl_str_mv Theoretical Study of 1,3-Dipolar Cycloadditions Regioselectivity of Benzyl Azide with Glycosyl-O Acetylene Using Density Functional Theory (DFT)
title Theoretical Study of 1,3-Dipolar Cycloadditions Regioselectivity of Benzyl Azide with Glycosyl-O Acetylene Using Density Functional Theory (DFT)
spellingShingle Theoretical Study of 1,3-Dipolar Cycloadditions Regioselectivity of Benzyl Azide with Glycosyl-O Acetylene Using Density Functional Theory (DFT)
Ghaleb, Adib
1,3-dipolar cycloadditions
1,2,3-triazole; regioselectivity
DFT calculations
Parr functions
title_short Theoretical Study of 1,3-Dipolar Cycloadditions Regioselectivity of Benzyl Azide with Glycosyl-O Acetylene Using Density Functional Theory (DFT)
title_full Theoretical Study of 1,3-Dipolar Cycloadditions Regioselectivity of Benzyl Azide with Glycosyl-O Acetylene Using Density Functional Theory (DFT)
title_fullStr Theoretical Study of 1,3-Dipolar Cycloadditions Regioselectivity of Benzyl Azide with Glycosyl-O Acetylene Using Density Functional Theory (DFT)
title_full_unstemmed Theoretical Study of 1,3-Dipolar Cycloadditions Regioselectivity of Benzyl Azide with Glycosyl-O Acetylene Using Density Functional Theory (DFT)
title_sort Theoretical Study of 1,3-Dipolar Cycloadditions Regioselectivity of Benzyl Azide with Glycosyl-O Acetylene Using Density Functional Theory (DFT)
dc.creator.none.fl_str_mv Ghaleb, Adib
Aouidate, Adnane
Sbai, Abdelouahid
Lakhlifi, Tahar
Maghat, Hamid
Bouachrine, Mohammed
author Ghaleb, Adib
author_facet Ghaleb, Adib
Aouidate, Adnane
Sbai, Abdelouahid
Lakhlifi, Tahar
Maghat, Hamid
Bouachrine, Mohammed
author_role author
author2 Aouidate, Adnane
Sbai, Abdelouahid
Lakhlifi, Tahar
Maghat, Hamid
Bouachrine, Mohammed
author2_role author
author
author
author
author
dc.subject.por.fl_str_mv 1,3-dipolar cycloadditions
1,2,3-triazole; regioselectivity
DFT calculations
Parr functions
topic 1,3-dipolar cycloadditions
1,2,3-triazole; regioselectivity
DFT calculations
Parr functions
description 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
publishDate 2017
dc.date.none.fl_str_mv 2017-12-29
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Peer-reviewed Article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv https://periodicos.ufms.br/index.php/orbital/article/view/16411
url https://periodicos.ufms.br/index.php/orbital/article/view/16411
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv https://periodicos.ufms.br/index.php/orbital/article/view/16411/11126
dc.rights.driver.fl_str_mv Copyright (c) 2017 Orbital: The Electronic Journal of Chemistry
https://creativecommons.org/licenses/by-nc-nd/4.0
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Copyright (c) 2017 Orbital: The Electronic Journal of Chemistry
https://creativecommons.org/licenses/by-nc-nd/4.0
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Instituto de Química, Universidade Federal de Mato Grosso do Sul
publisher.none.fl_str_mv Instituto de Química, Universidade Federal de Mato Grosso do Sul
dc.source.none.fl_str_mv Orbital: The Electronic Journal of Chemistry; Orbital - Vol. 9 No. 5 - October - December 2017; 337-343
Orbital: The Electronic Journal of Chemistry; Orbital - Vol. 9 No. 5 - October - December 2017; 337-343
1984-6428
reponame:Orbital - The Electronic Journal of Chemistry (Campo Grande)
instname:Universidade Federal de Mato Grosso do Sul (UFMS)
instacron:UFMS
instname_str Universidade Federal de Mato Grosso do Sul (UFMS)
instacron_str UFMS
institution UFMS
reponame_str Orbital - The Electronic Journal of Chemistry (Campo Grande)
collection Orbital - The Electronic Journal of Chemistry (Campo Grande)
repository.name.fl_str_mv Orbital - The Electronic Journal of Chemistry (Campo Grande) - Universidade Federal de Mato Grosso do Sul (UFMS)
repository.mail.fl_str_mv editor.orbital@ufms.br || marcos.amaral@ufms.br
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score 15,300719

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