Theoretical study of acetylation of ethylamine catalyzed by Mn2+ions

Autores
Caglieri, Silvana; Servetti, Gustavo Iván
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A theoretical study of acetylation of ethylamine catalyzed by Mn2+ 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. In the present theoretical work were investigated the structure and energy of the tetrahedral intermediate of the reaction catalyzed by Mn2+ 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 66.42 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 17.45 kcal/mol.
Fil: Caglieri, Silvana. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.
Fil: Servetti, Gustavo Ivàn. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.
Peer Reviewed
Materia
Acetylation of ethylamine
Organic synthesis
Nucleophilic substitution
Nivel de accesibilidad
acceso abierto
Condiciones de uso
2024-07-29T21:49:27Z
Repositorio
Repositorio Institucional Abierto (UTN)
Institución
Universidad Tecnológica Nacional
OAI Identificador
oai:ria.utn.edu.ar:20.500.12272/11185
Acceder
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network_acronym_str RIAUTN
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network_name_str Repositorio Institucional Abierto (UTN)
spelling Theoretical study of acetylation of ethylamine catalyzed by Mn2+ionsCaglieri, SilvanaServetti, Gustavo IvánAcetylation of ethylamineOrganic synthesisNucleophilic substitutionA theoretical study of acetylation of ethylamine catalyzed by Mn2+ 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. In the present theoretical work were investigated the structure and energy of the tetrahedral intermediate of the reaction catalyzed by Mn2+ 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 66.42 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 17.45 kcal/mol.Fil: Caglieri, Silvana. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.Fil: Servetti, Gustavo Ivàn. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.Peer Reviewed2024-07-29T21:49:27Z2024-07-29T21:49:27Z2015info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articulopdfapplication/pdfInternational Chemical Congress of Pacific Basin Societies.2015http://hdl.handle.net/20.500.12272/11185-enginfo:eu-repo/semantics/openAccess2024-07-29T21:49:27Zhttp://creativecommons.org/licenses/by-nc-nd/4.0/Attribution-NonCommercial-NoDerivatives 4.0 InternacionalCaglieri, Silvana; Servetti, Gustavo Ivànhttps://creativecommons.org/licenses/by-nc-sa/4.0/reponame:Repositorio Institucional Abierto (UTN)instname:Universidad Tecnológica Nacional2026-10-01T11:58:21Zoai:ria.utn.edu.ar:20.500.12272/11185instacron: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:a2026-10-01 11:58:22.469Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacionalfalse
dc.title.none.fl_str_mv Theoretical study of acetylation of ethylamine catalyzed by Mn2+ions
title Theoretical study of acetylation of ethylamine catalyzed by Mn2+ions
spellingShingle Theoretical study of acetylation of ethylamine catalyzed by Mn2+ions
Caglieri, Silvana
Acetylation of ethylamine
Organic synthesis
Nucleophilic substitution
title_short Theoretical study of acetylation of ethylamine catalyzed by Mn2+ions
title_full Theoretical study of acetylation of ethylamine catalyzed by Mn2+ions
title_fullStr Theoretical study of acetylation of ethylamine catalyzed by Mn2+ions
title_full_unstemmed Theoretical study of acetylation of ethylamine catalyzed by Mn2+ions
title_sort Theoretical study of acetylation of ethylamine catalyzed by Mn2+ions
dc.creator.none.fl_str_mv Caglieri, Silvana
Servetti, Gustavo Iván
author Caglieri, Silvana
author_facet Caglieri, Silvana
Servetti, Gustavo Iván
author_role author
author2 Servetti, Gustavo Iván
author2_role author
dc.subject.none.fl_str_mv Acetylation of ethylamine
Organic synthesis
Nucleophilic substitution
topic Acetylation of ethylamine
Organic synthesis
Nucleophilic substitution
dc.description.none.fl_txt_mv A theoretical study of acetylation of ethylamine catalyzed by Mn2+ 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. In the present theoretical work were investigated the structure and energy of the tetrahedral intermediate of the reaction catalyzed by Mn2+ 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 66.42 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 17.45 kcal/mol.
Fil: Caglieri, Silvana. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.
Fil: Servetti, Gustavo Ivàn. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.
Peer Reviewed
description A theoretical study of acetylation of ethylamine catalyzed by Mn2+ 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. In the present theoretical work were investigated the structure and energy of the tetrahedral intermediate of the reaction catalyzed by Mn2+ 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 66.42 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 17.45 kcal/mol.
publishDate 2015
dc.date.none.fl_str_mv 2015
2024-07-29T21:49:27Z
2024-07-29T21:49:27Z
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 International Chemical Congress of Pacific Basin Societies.2015
http://hdl.handle.net/20.500.12272/11185
-
identifier_str_mv International Chemical Congress of Pacific Basin Societies.2015
-
url http://hdl.handle.net/20.500.12272/11185
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
2024-07-29T21:49:27Z
http://creativecommons.org/licenses/by-nc-nd/4.0/
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
Caglieri, Silvana; Servetti, Gustavo Ivàn
https://creativecommons.org/licenses/by-nc-sa/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv 2024-07-29T21:49:27Z
http://creativecommons.org/licenses/by-nc-nd/4.0/
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
Caglieri, Silvana; Servetti, Gustavo Ivàn
https://creativecommons.org/licenses/by-nc-sa/4.0/
dc.format.none.fl_str_mv pdf
application/pdf
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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