DFT Studies on the Stereoselective Three-Component Ugi Reaction

studied theoretically based on DFT calculations. Structures of reagents, products, intermediates, and transition states were optimized at M062X/6-31+g(d,p) level of theory in gas phase and in methanol as a common solvent for this reaction. The reaction takes place through several processes, includin...

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Detalles Bibliográficos
Autores: Sharifzadeh, Elaheh Sadat, Shiraz, Nader Zabarjad
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2019
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/16004
Acceso en línea:https://periodicos.ufms.br/index.php/orbital/article/view/16004
Access Level:acceso abierto
Palabra clave:DFT calculation
multicomponent reaction
stereoselectivity
three-component Ugi reaction
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spelling DFT Studies on the Stereoselective Three-Component Ugi ReactionDFT calculationmulticomponent reactionstereoselectivitythree-component Ugi reactionstudied theoretically based on DFT calculations. Structures of reagents, products, intermediates, and transition states were optimized at M062X/6-31+g(d,p) level of theory in gas phase and in methanol as a common solvent for this reaction. The reaction takes place through several processes, including atom inversion, bond rotation, acid-base, nucleophile-electrophile competitions. These diverse phenomena were studied to provide a clearer picture of the mechanism of this valuable reaction, especially in terms of stereochemistry considerations. According to the results, the enthalpy of the reaction was -45.9 and -41.2 kcal/mol for the dominant product in gas phase and in methanol. The stereoselectivity of the reaction was under the kinetic control of nucleophilic attack of isocyanide to less hindered si-face (Ea= 4.1       compared to 7.4 kcal/mol for re-face) of more stable chiral (E)-iminium in methanol. DOI: http://dx.doi.org/10.17807/orbital.v11i1.1214Instituto de Química, Universidade Federal de Mato Grosso do Sul2019-03-30info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionPeer-reviewed Articleapplication/pdfhttps://periodicos.ufms.br/index.php/orbital/article/view/16004Orbital: The Electronic Journal of Chemistry; Orbital - Vol. 11 No. 1 - January-March 2019; 18-24Orbital: The Electronic Journal of Chemistry; Orbital - Vol. 11 No. 1 - January-March 2019; 18-241984-6428reponame: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/16004/10927Copyright (c) 2019 Orbital: The Electronic Journal of Chemistryhttps://creativecommons.org/licenses/by-nc-nd/4.0info:eu-repo/semantics/openAccessSharifzadeh, Elaheh SadatShiraz, Nader Zabarjad2023-01-20T10:53:29Zoai:periodicos.ufms.br:article/16004Revistahttps://periodicos.ufms.br/index.php/orbital/indexPUBhttps://periodicos.ufms.br/index.php/orbital/oaieditor.orbital@ufms.br || marcos.amaral@ufms.br1984-64281984-6428opendoar:2023-01-20T10:53:29Orbital - The Electronic Journal of Chemistry (Campo Grande) - Universidade Federal de Mato Grosso do Sul (UFMS)false
dc.title.none.fl_str_mv DFT Studies on the Stereoselective Three-Component Ugi Reaction
title DFT Studies on the Stereoselective Three-Component Ugi Reaction
spellingShingle DFT Studies on the Stereoselective Three-Component Ugi Reaction
Sharifzadeh, Elaheh Sadat
DFT calculation
multicomponent reaction
stereoselectivity
three-component Ugi reaction
title_short DFT Studies on the Stereoselective Three-Component Ugi Reaction
title_full DFT Studies on the Stereoselective Three-Component Ugi Reaction
title_fullStr DFT Studies on the Stereoselective Three-Component Ugi Reaction
title_full_unstemmed DFT Studies on the Stereoselective Three-Component Ugi Reaction
title_sort DFT Studies on the Stereoselective Three-Component Ugi Reaction
dc.creator.none.fl_str_mv Sharifzadeh, Elaheh Sadat
Shiraz, Nader Zabarjad
author Sharifzadeh, Elaheh Sadat
author_facet Sharifzadeh, Elaheh Sadat
Shiraz, Nader Zabarjad
author_role author
author2 Shiraz, Nader Zabarjad
author2_role author
dc.subject.por.fl_str_mv DFT calculation
multicomponent reaction
stereoselectivity
three-component Ugi reaction
topic DFT calculation
multicomponent reaction
stereoselectivity
three-component Ugi reaction
description studied theoretically based on DFT calculations. Structures of reagents, products, intermediates, and transition states were optimized at M062X/6-31+g(d,p) level of theory in gas phase and in methanol as a common solvent for this reaction. The reaction takes place through several processes, including atom inversion, bond rotation, acid-base, nucleophile-electrophile competitions. These diverse phenomena were studied to provide a clearer picture of the mechanism of this valuable reaction, especially in terms of stereochemistry considerations. According to the results, the enthalpy of the reaction was -45.9 and -41.2 kcal/mol for the dominant product in gas phase and in methanol. The stereoselectivity of the reaction was under the kinetic control of nucleophilic attack of isocyanide to less hindered si-face (Ea= 4.1       compared to 7.4 kcal/mol for re-face) of more stable chiral (E)-iminium in methanol. DOI: http://dx.doi.org/10.17807/orbital.v11i1.1214
publishDate 2019
dc.date.none.fl_str_mv 2019-03-30
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/16004
url https://periodicos.ufms.br/index.php/orbital/article/view/16004
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv https://periodicos.ufms.br/index.php/orbital/article/view/16004/10927
dc.rights.driver.fl_str_mv Copyright (c) 2019 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) 2019 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. 11 No. 1 - January-March 2019; 18-24
Orbital: The Electronic Journal of Chemistry; Orbital - Vol. 11 No. 1 - January-March 2019; 18-24
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 15,300724

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