Theoretical study of acid acetylation of ethylamine

Autores
Caglieri, Silvana
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Abstract. The acetylation of amines 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 Brönsted acid. In the mechanism, the acetic anhydride first accepts a proton at the carbonyl oxygen and this change enhances the positive charge on the carbonyl carbon. This protonation facilitates the successive addition of amine at the position to form a tetrahedral intermediate, determining step of the rate of the reaction. Computational method to study the reaction using acid catalysis [1] and an experimental work [2], agreed that this reaction takes place with the formation of a tetrahedral intermediate. A theoretical study of acid acetylation of ethylamine from the analysis of intermediate of the reaction was carried out. 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 - Density Functional Theory [3] with B3LYP level of theory and was adopted the 3-21+G* basis set. Energies of all reagents and products and the energy of activation for the reaction were calculated using the AM1- Austin Model 1 method. Following the same procedure it was identified the geometric parameters and energy of intermediate. All the calculations were executed using Gaussian 09 software package. The calculations show 33.89 kcal/mol of energy for the tetrahedral intermediate and the activation energy was 9.07 kcal/mol. It was observed a marked consistency between the theoretical results and bibliographic data, which validates the use of theoretical methods DFT and AM1 as tools for kinetic studying the reaction of acetylation of ethylamine.
Fil: Caglieri, Silvana. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.
Peer Reviewed
Materia
Acetylation
Ethylamine
AM1
DFT
Nivel de accesibilidad
acceso abierto
Condiciones de uso
2024-07-23T20:35:54Z
Repositorio
Repositorio Institucional Abierto (UTN)
Institución
Universidad Tecnológica Nacional
OAI Identificador
oai:ria.utn.edu.ar:20.500.12272/11153
Acceder
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network_acronym_str RIAUTN
repository_id_str a
network_name_str Repositorio Institucional Abierto (UTN)
spelling Theoretical study of acid acetylation of ethylamineCaglieri, SilvanaAcetylationEthylamineAM1DFTAbstract. The acetylation of amines 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 Brönsted acid. In the mechanism, the acetic anhydride first accepts a proton at the carbonyl oxygen and this change enhances the positive charge on the carbonyl carbon. This protonation facilitates the successive addition of amine at the position to form a tetrahedral intermediate, determining step of the rate of the reaction. Computational method to study the reaction using acid catalysis [1] and an experimental work [2], agreed that this reaction takes place with the formation of a tetrahedral intermediate. A theoretical study of acid acetylation of ethylamine from the analysis of intermediate of the reaction was carried out. 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 - Density Functional Theory [3] with B3LYP level of theory and was adopted the 3-21+G* basis set. Energies of all reagents and products and the energy of activation for the reaction were calculated using the AM1- Austin Model 1 method. Following the same procedure it was identified the geometric parameters and energy of intermediate. All the calculations were executed using Gaussian 09 software package. The calculations show 33.89 kcal/mol of energy for the tetrahedral intermediate and the activation energy was 9.07 kcal/mol. It was observed a marked consistency between the theoretical results and bibliographic data, which validates the use of theoretical methods DFT and AM1 as tools for kinetic studying the reaction of acetylation of ethylamine.Fil: Caglieri, Silvana. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.Peer Reviewed2024-07-23T20:35:54Z2024-07-23T20:35:54Z2014info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articulopdfapplication/pdfXL Congreso de Quìmicos Teòricos de Expresiòn Latina.2014http://hdl.handle.net/20.500.12272/11153-enginfo:eu-repo/semantics/openAccess2024-07-23T20:35:54Zhttp://creativecommons.org/licenses/by-nc-nd/4.0/Attribution-NonCommercial-NoDerivatives 4.0 InternacionalCaglieri , Silvanahttps://creativecommons.org/licenses/by-nc-sa/4.0/reponame:Repositorio Institucional Abierto (UTN)instname:Universidad Tecnológica Nacional2026-09-24T12:45:46Zoai:ria.utn.edu.ar:20.500.12272/11153instacron: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 12:45:48.515Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacionalfalse
dc.title.none.fl_str_mv Theoretical study of acid acetylation of ethylamine
title Theoretical study of acid acetylation of ethylamine
spellingShingle Theoretical study of acid acetylation of ethylamine
Caglieri, Silvana
Acetylation
Ethylamine
AM1
DFT
title_short Theoretical study of acid acetylation of ethylamine
title_full Theoretical study of acid acetylation of ethylamine
title_fullStr Theoretical study of acid acetylation of ethylamine
title_full_unstemmed Theoretical study of acid acetylation of ethylamine
title_sort Theoretical study of acid acetylation of ethylamine
dc.creator.none.fl_str_mv Caglieri, Silvana
author Caglieri, Silvana
author_facet Caglieri, Silvana
author_role author
dc.subject.none.fl_str_mv Acetylation
Ethylamine
AM1
DFT
topic Acetylation
Ethylamine
AM1
DFT
dc.description.none.fl_txt_mv Abstract. The acetylation of amines 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 Brönsted acid. In the mechanism, the acetic anhydride first accepts a proton at the carbonyl oxygen and this change enhances the positive charge on the carbonyl carbon. This protonation facilitates the successive addition of amine at the position to form a tetrahedral intermediate, determining step of the rate of the reaction. Computational method to study the reaction using acid catalysis [1] and an experimental work [2], agreed that this reaction takes place with the formation of a tetrahedral intermediate. A theoretical study of acid acetylation of ethylamine from the analysis of intermediate of the reaction was carried out. 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 - Density Functional Theory [3] with B3LYP level of theory and was adopted the 3-21+G* basis set. Energies of all reagents and products and the energy of activation for the reaction were calculated using the AM1- Austin Model 1 method. Following the same procedure it was identified the geometric parameters and energy of intermediate. All the calculations were executed using Gaussian 09 software package. The calculations show 33.89 kcal/mol of energy for the tetrahedral intermediate and the activation energy was 9.07 kcal/mol. It was observed a marked consistency between the theoretical results and bibliographic data, which validates the use of theoretical methods DFT and AM1 as tools for kinetic studying the reaction of acetylation of ethylamine.
Fil: Caglieri, Silvana. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.
Peer Reviewed
description Abstract. The acetylation of amines 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 Brönsted acid. In the mechanism, the acetic anhydride first accepts a proton at the carbonyl oxygen and this change enhances the positive charge on the carbonyl carbon. This protonation facilitates the successive addition of amine at the position to form a tetrahedral intermediate, determining step of the rate of the reaction. Computational method to study the reaction using acid catalysis [1] and an experimental work [2], agreed that this reaction takes place with the formation of a tetrahedral intermediate. A theoretical study of acid acetylation of ethylamine from the analysis of intermediate of the reaction was carried out. 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 - Density Functional Theory [3] with B3LYP level of theory and was adopted the 3-21+G* basis set. Energies of all reagents and products and the energy of activation for the reaction were calculated using the AM1- Austin Model 1 method. Following the same procedure it was identified the geometric parameters and energy of intermediate. All the calculations were executed using Gaussian 09 software package. The calculations show 33.89 kcal/mol of energy for the tetrahedral intermediate and the activation energy was 9.07 kcal/mol. It was observed a marked consistency between the theoretical results and bibliographic data, which validates the use of theoretical methods DFT and AM1 as tools for kinetic studying the reaction of acetylation of ethylamine.
publishDate 2014
dc.date.none.fl_str_mv 2014
2024-07-23T20:35:54Z
2024-07-23T20:35:54Z
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 XL Congreso de Quìmicos Teòricos de Expresiòn Latina.2014
http://hdl.handle.net/20.500.12272/11153
-
identifier_str_mv XL Congreso de Quìmicos Teòricos de Expresiòn Latina.2014
-
url http://hdl.handle.net/20.500.12272/11153
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
2024-07-23T20:35:54Z
http://creativecommons.org/licenses/by-nc-nd/4.0/
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
Caglieri , Silvana
https://creativecommons.org/licenses/by-nc-sa/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv 2024-07-23T20:35:54Z
http://creativecommons.org/licenses/by-nc-nd/4.0/
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
Caglieri , Silvana
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)
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instname_str Universidad Tecnológica Nacional
repository.name.fl_str_mv Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacional
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