Theoretical study of p-nitrophenol acetylation catalyzed by Co2+ions

Autores
Caglieri, Silvana Claudia
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión aceptada
Descripción
A theoretical study of acetylation of p-nitrophenol catalyzed by Co2+ ions from the analysis of intermediate of the reaction was carried out. The study of acetylation of alcohols is of great interest by the utility of its products of reaction and is one of the most frequently used transformations in organic synthesis as it provides an efficient means for protecting hydroxyl groups in a synthetic process. Acetylation of alcohols is a nucleophilic substitution reaction. This reaction can be catalyzed by Lewis acid, metallic ion. In reaction mechanism, the metallic ion formed a complex with the oxygen of the acetic anhydride carbonyl, facilitating the polarization of the same and the successive addition of alcohol at the position to form a tetrahedral intermediate, determining step of the rate of the reaction. Experimental studies were carried out and agreed that this reaction takes place with the formation of a tetrahedral intermediate. In the present theoretical work were investigated the structure and energy of the tetrahedral intermediate of the reaction catalyzed by Co2+ ions. Geometries of all species involved in the acetylation were made and identified. All of the geometry optimizations were performed by the method at the DFT/B3LYP level of theory and were adopted the 6-31+G* basis sets. Energies were calculated using the Mechanics-UFF method. Following the same procedure it was identified the geometric parameters and energy of reaction intermediate. The calculations show 79.32 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 30.31 kcal/mol.
Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Peer Reviewed
Fuente
Revista de catálisis molecular A: Química Volumen 407 ,octubre de 2015, páginas 102-112.
Materia
acetylation
p-nitrophenol
Hidroxil groups
Nivel de accesibilidad
acceso abierto
Condiciones de uso
Attribution-NonCommercial-NoDerivs 2.5 Argentina
Repositorio
Repositorio Institucional Abierto (UTN)
Institución
Universidad Tecnológica Nacional
OAI Identificador
oai:ria.utn.edu.ar:20.500.12272/15203
Acceder
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network_acronym_str RIAUTN
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network_name_str Repositorio Institucional Abierto (UTN)
spelling Theoretical study of p-nitrophenol acetylation catalyzed by Co2+ionsCaglieri, Silvana Claudiaacetylationp-nitrophenolHidroxil groupsA theoretical study of acetylation of p-nitrophenol catalyzed by Co2+ ions from the analysis of intermediate of the reaction was carried out. The study of acetylation of alcohols is of great interest by the utility of its products of reaction and is one of the most frequently used transformations in organic synthesis as it provides an efficient means for protecting hydroxyl groups in a synthetic process. Acetylation of alcohols is a nucleophilic substitution reaction. This reaction can be catalyzed by Lewis acid, metallic ion. In reaction mechanism, the metallic ion formed a complex with the oxygen of the acetic anhydride carbonyl, facilitating the polarization of the same and the successive addition of alcohol at the position to form a tetrahedral intermediate, determining step of the rate of the reaction. Experimental studies were carried out and agreed that this reaction takes place with the formation of a tetrahedral intermediate. In the present theoretical work were investigated the structure and energy of the tetrahedral intermediate of the reaction catalyzed by Co2+ ions. Geometries of all species involved in the acetylation were made and identified. All of the geometry optimizations were performed by the method at the DFT/B3LYP level of theory and were adopted the 6-31+G* basis sets. Energies were calculated using the Mechanics-UFF method. Following the same procedure it was identified the geometric parameters and energy of reaction intermediate. The calculations show 79.32 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 30.31 kcal/mol.Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.Peer ReviewedElsevier2026-06-17T19:09:19Z2015info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articulopdfapplication/pdfRevista de catálisis molecular A: Químicahttps://hdl.handle.net/20.500.12272/15203https://doi.org/10.1016/j.molcata.2015.06.024Revista de catálisis molecular A: Química Volumen 407 ,octubre de 2015, páginas 102-112.reponame:Repositorio Institucional Abierto (UTN)instname:Universidad Tecnológica Nacionalenginfo:eu-repo/semantics/openAccessAttribution-NonCommercial-NoDerivs 2.5 Argentinahttp://creativecommons.org/licenses/by-nc-nd/2.5/ar/Caglieri, Silvana Claudia.https://creativecommons.org/licenses/by-nc-nd/4.0/2026-09-24T12:44:19Zoai:ria.utn.edu.ar:20.500.12272/15203instacron:UTNInstitucionalhttp://ria.utn.edu.ar/Universidad públicaNo correspondehttp://ria.utn.edu.ar/oaigestionria@rec.utn.edu.ar; fsuarez@rec.utn.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:a2026-09-24 12:44:21.041Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacionalfalse
dc.title.none.fl_str_mv Theoretical study of p-nitrophenol acetylation catalyzed by Co2+ions
title Theoretical study of p-nitrophenol acetylation catalyzed by Co2+ions
spellingShingle Theoretical study of p-nitrophenol acetylation catalyzed by Co2+ions
Caglieri, Silvana Claudia
acetylation
p-nitrophenol
Hidroxil groups
title_short Theoretical study of p-nitrophenol acetylation catalyzed by Co2+ions
title_full Theoretical study of p-nitrophenol acetylation catalyzed by Co2+ions
title_fullStr Theoretical study of p-nitrophenol acetylation catalyzed by Co2+ions
title_full_unstemmed Theoretical study of p-nitrophenol acetylation catalyzed by Co2+ions
title_sort Theoretical study of p-nitrophenol acetylation catalyzed by Co2+ions
dc.creator.none.fl_str_mv Caglieri, Silvana Claudia
author Caglieri, Silvana Claudia
author_facet Caglieri, Silvana Claudia
author_role author
dc.subject.none.fl_str_mv acetylation
p-nitrophenol
Hidroxil groups
topic acetylation
p-nitrophenol
Hidroxil groups
dc.description.none.fl_txt_mv A theoretical study of acetylation of p-nitrophenol catalyzed by Co2+ ions from the analysis of intermediate of the reaction was carried out. The study of acetylation of alcohols is of great interest by the utility of its products of reaction and is one of the most frequently used transformations in organic synthesis as it provides an efficient means for protecting hydroxyl groups in a synthetic process. Acetylation of alcohols is a nucleophilic substitution reaction. This reaction can be catalyzed by Lewis acid, metallic ion. In reaction mechanism, the metallic ion formed a complex with the oxygen of the acetic anhydride carbonyl, facilitating the polarization of the same and the successive addition of alcohol at the position to form a tetrahedral intermediate, determining step of the rate of the reaction. Experimental studies were carried out and agreed that this reaction takes place with the formation of a tetrahedral intermediate. In the present theoretical work were investigated the structure and energy of the tetrahedral intermediate of the reaction catalyzed by Co2+ ions. Geometries of all species involved in the acetylation were made and identified. All of the geometry optimizations were performed by the method at the DFT/B3LYP level of theory and were adopted the 6-31+G* basis sets. Energies were calculated using the Mechanics-UFF method. Following the same procedure it was identified the geometric parameters and energy of reaction intermediate. The calculations show 79.32 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 30.31 kcal/mol.
Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Peer Reviewed
description A theoretical study of acetylation of p-nitrophenol catalyzed by Co2+ ions from the analysis of intermediate of the reaction was carried out. The study of acetylation of alcohols is of great interest by the utility of its products of reaction and is one of the most frequently used transformations in organic synthesis as it provides an efficient means for protecting hydroxyl groups in a synthetic process. Acetylation of alcohols is a nucleophilic substitution reaction. This reaction can be catalyzed by Lewis acid, metallic ion. In reaction mechanism, the metallic ion formed a complex with the oxygen of the acetic anhydride carbonyl, facilitating the polarization of the same and the successive addition of alcohol at the position to form a tetrahedral intermediate, determining step of the rate of the reaction. Experimental studies were carried out and agreed that this reaction takes place with the formation of a tetrahedral intermediate. In the present theoretical work were investigated the structure and energy of the tetrahedral intermediate of the reaction catalyzed by Co2+ ions. Geometries of all species involved in the acetylation were made and identified. All of the geometry optimizations were performed by the method at the DFT/B3LYP level of theory and were adopted the 6-31+G* basis sets. Energies were calculated using the Mechanics-UFF method. Following the same procedure it was identified the geometric parameters and energy of reaction intermediate. The calculations show 79.32 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 30.31 kcal/mol.
publishDate 2015
dc.date.none.fl_str_mv 2015
2026-06-17T19:09:19Z
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv Revista de catálisis molecular A: Química
https://hdl.handle.net/20.500.12272/15203
https://doi.org/10.1016/j.molcata.2015.06.024
identifier_str_mv Revista de catálisis molecular A: Química
url https://hdl.handle.net/20.500.12272/15203
https://doi.org/10.1016/j.molcata.2015.06.024
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
Attribution-NonCommercial-NoDerivs 2.5 Argentina
http://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Caglieri, Silvana Claudia.
https://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivs 2.5 Argentina
http://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Caglieri, Silvana Claudia.
https://creativecommons.org/licenses/by-nc-nd/4.0/
dc.format.none.fl_str_mv pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv Revista de catálisis molecular A: Química Volumen 407 ,octubre de 2015, páginas 102-112.
reponame:Repositorio Institucional Abierto (UTN)
instname:Universidad Tecnológica Nacional
reponame_str Repositorio Institucional Abierto (UTN)
collection Repositorio Institucional Abierto (UTN)
instname_str Universidad Tecnológica Nacional
repository.name.fl_str_mv Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacional
repository.mail.fl_str_mv gestionria@rec.utn.edu.ar; fsuarez@rec.utn.edu.ar
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