Theoretical study of aniline acetylation catalyzed by Cu2+ IONS

Autores
Caglieri, Silvana Claudia; Macaño, Héctor Rubén; Servetti, Gustavo Iván
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Theoretical study of aniline acetylation 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 synthetic process. Acetylation of amine is a nucleophilic substitution reaction. This reaction can be catalyzed by Lewis acid1, 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 work2 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 was 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 Figure show the optimized structure of the intermediate and the calculations show 73.84 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 20.46 kcal/mol. Tetrahedral Intermediate
Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Fil: Macaño, Héctor Rubén. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Fil: Servetti, Gustavo Iván. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Peer Reviewed
Materia
Acetilation of amines
Nucleophilic substitution
DFT/B3LYP
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:20.500.12272/15490
Acceder
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network_acronym_str RIAUTN
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network_name_str Repositorio Institucional Abierto (UTN)
spelling Theoretical study of aniline acetylation catalyzed by Cu2+ IONSCaglieri, Silvana ClaudiaMacaño, Héctor RubénServetti, Gustavo IvánAcetilation of aminesNucleophilic substitutionDFT/B3LYPTheoretical study of aniline acetylation 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 synthetic process. Acetylation of amine is a nucleophilic substitution reaction. This reaction can be catalyzed by Lewis acid1, 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 work2 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 was 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 Figure show the optimized structure of the intermediate and the calculations show 73.84 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 20.46 kcal/mol. Tetrahedral IntermediateFil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.Fil: Macaño, Héctor Rubén. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.Fil: Servetti, Gustavo Iván. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.Peer ReviewedUniversitat Jaume I2026-09-04T21:57:30Z2016info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articulopdfapplication/pdf10th Congress on Electronic Structure. 2016https://hdl.handle.net/20.500.12272/15490enginfo:eu-repo/semantics/openAccessAttribution-NonCommercial-NoDerivs 2.5 Argentinahttp://creativecommons.org/licenses/by-nc-nd/2.5/ar/Caglieri, Silvana Claudia; Macaño, Héctor Rubén; Servetti, Gustavo Ivánhttps://creativecommons.org/licenses/by-nc-nd/4.0/reponame:Repositorio Institucional Abierto (UTN)instname:Universidad Tecnológica Nacional2026-09-24T12:44:00Zoai:ria.utn.edu.ar:20.500.12272/15490instacron: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 12:44:02.376Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacionalfalse
dc.title.none.fl_str_mv Theoretical study of aniline acetylation catalyzed by Cu2+ IONS
title Theoretical study of aniline acetylation catalyzed by Cu2+ IONS
spellingShingle Theoretical study of aniline acetylation catalyzed by Cu2+ IONS
Caglieri, Silvana Claudia
Acetilation of amines
Nucleophilic substitution
DFT/B3LYP
title_short Theoretical study of aniline acetylation catalyzed by Cu2+ IONS
title_full Theoretical study of aniline acetylation catalyzed by Cu2+ IONS
title_fullStr Theoretical study of aniline acetylation catalyzed by Cu2+ IONS
title_full_unstemmed Theoretical study of aniline acetylation catalyzed by Cu2+ IONS
title_sort Theoretical study of aniline acetylation catalyzed by Cu2+ IONS
dc.creator.none.fl_str_mv Caglieri, Silvana Claudia
Macaño, Héctor Rubén
Servetti, Gustavo Iván
author Caglieri, Silvana Claudia
author_facet Caglieri, Silvana Claudia
Macaño, Héctor Rubén
Servetti, Gustavo Iván
author_role author
author2 Macaño, Héctor Rubén
Servetti, Gustavo Iván
author2_role author
author
dc.subject.none.fl_str_mv Acetilation of amines
Nucleophilic substitution
DFT/B3LYP
topic Acetilation of amines
Nucleophilic substitution
DFT/B3LYP
dc.description.none.fl_txt_mv Theoretical study of aniline acetylation 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 synthetic process. Acetylation of amine is a nucleophilic substitution reaction. This reaction can be catalyzed by Lewis acid1, 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 work2 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 was 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 Figure show the optimized structure of the intermediate and the calculations show 73.84 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 20.46 kcal/mol. Tetrahedral Intermediate
Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Fil: Macaño, Héctor Rubén. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Fil: Servetti, Gustavo Iván. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Peer Reviewed
description Theoretical study of aniline acetylation 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 synthetic process. Acetylation of amine is a nucleophilic substitution reaction. This reaction can be catalyzed by Lewis acid1, 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 work2 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 was 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 Figure show the optimized structure of the intermediate and the calculations show 73.84 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 20.46 kcal/mol. Tetrahedral Intermediate
publishDate 2016
dc.date.none.fl_str_mv 2016
2026-09-04T21:57:30Z
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 10th Congress on Electronic Structure. 2016
https://hdl.handle.net/20.500.12272/15490
identifier_str_mv 10th Congress on Electronic Structure. 2016
url https://hdl.handle.net/20.500.12272/15490
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; Macaño, Héctor Rubén; Servetti, Gustavo Iván
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; Macaño, Héctor Rubén; Servetti, Gustavo Iván
https://creativecommons.org/licenses/by-nc-nd/4.0/
dc.format.none.fl_str_mv pdf
application/pdf
dc.publisher.none.fl_str_mv Universitat Jaume I
publisher.none.fl_str_mv Universitat Jaume I
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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