Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ ions

Autores
Caglieri, Silvana Claudia
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ ions from the analysis of intermediate of the reaction was carried out. The study of acetylation of amines 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 and inexpensive means for protecting amino groups in a multistep synthetic process. Acetylation of amine 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 amine at the position to form a tetrahedral intermediate, determining step of the rate of the reaction. Experimental work 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 Cu2+ 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 the method MP2. 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 61.35 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 15.55 kcal/mol.
Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Peer Reviewed
Materia
Amides
Amines
DFT
MP2
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:20.500.12272/15588
Acceder
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network_acronym_str RIAUTN
repository_id_str a
network_name_str Repositorio Institucional Abierto (UTN)
spelling Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ ionsCaglieri, Silvana ClaudiaAmidesAminesDFTMP2Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ ions from the analysis of intermediate of the reaction was carried out. The study of acetylation of amines 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 and inexpensive means for protecting amino groups in a multistep synthetic process. Acetylation of amine 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 amine at the position to form a tetrahedral intermediate, determining step of the rate of the reaction. Experimental work 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 Cu2+ 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 the method MP2. 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 61.35 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 15.55 kcal/mol.Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.Peer ReviewedWorld Academy of Science, Engineering and Technology2026-09-15T23:41:40Z2017info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articulopdfapplication/pdf19Th International Conference on Neural Science and Engineering. 2017https://hdl.handle.net/20.500.12272/15588enginfo:eu-repo/semantics/openAccessAttribution-NonCommercial-NoDerivs 2.5 Argentinahttp://creativecommons.org/licenses/by-nc-nd/2.5/ar/Caglieri, Silvana Claudiahttps://creativecommons.org/licenses/by-nc-nd/4.0/reponame:Repositorio Institucional Abierto (UTN)instname:Universidad Tecnológica Nacional2026-09-24T12:45:05Zoai:ria.utn.edu.ar:20.500.12272/15588instacron: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 12:45:06.436Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacionalfalse
dc.title.none.fl_str_mv Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ ions
title Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ ions
spellingShingle Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ ions
Caglieri, Silvana Claudia
Amides
Amines
DFT
MP2
title_short Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ ions
title_full Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ ions
title_fullStr Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ ions
title_full_unstemmed Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ ions
title_sort Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ 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 Amides
Amines
DFT
MP2
topic Amides
Amines
DFT
MP2
dc.description.none.fl_txt_mv Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ ions from the analysis of intermediate of the reaction was carried out. The study of acetylation of amines 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 and inexpensive means for protecting amino groups in a multistep synthetic process. Acetylation of amine 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 amine at the position to form a tetrahedral intermediate, determining step of the rate of the reaction. Experimental work 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 Cu2+ 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 the method MP2. 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 61.35 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 15.55 kcal/mol.
Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Peer Reviewed
description Theoretical study of acetylation of p-methylaniline catalyzed by Cu2+ ions from the analysis of intermediate of the reaction was carried out. The study of acetylation of amines 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 and inexpensive means for protecting amino groups in a multistep synthetic process. Acetylation of amine 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 amine at the position to form a tetrahedral intermediate, determining step of the rate of the reaction. Experimental work 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 Cu2+ 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 the method MP2. 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 61.35 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 15.55 kcal/mol.
publishDate 2017
dc.date.none.fl_str_mv 2017
2026-09-15T23:41:40Z
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv 19Th International Conference on Neural Science and Engineering. 2017
https://hdl.handle.net/20.500.12272/15588
identifier_str_mv 19Th International Conference on Neural Science and Engineering. 2017
url https://hdl.handle.net/20.500.12272/15588
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 World Academy of Science, Engineering and Technology
publisher.none.fl_str_mv World Academy of Science, Engineering and Technology
dc.source.none.fl_str_mv 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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score 13.24418

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