Theoretical study of acid acetylation of aniline

Autores
Caglieri, Silvana; Servetti, Gustavo Iván; Picco, Eduardo
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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 aniline 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 6-31G* basis set. Energies of all reagents and products and the energy of activation for the reaction were calculated using the MP2- 2nd order Mo/ller–Plesset method. Following the same procedure it was identified the geometric parameters and energy of intermediate. Figure 1 show the optimized structure of the intermediate and the Table 1 lists the geometric parameters, lengths and binding angles values, obtained. The calculations show 18.37 kcal/mol of activation energy.
Fil: Caglieri, Silvana. Universidad Tecnológica Nacional . Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.
Fil: Servetti, Gustavo Iván. Universidad Tecnológica Nacional . Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.
Fil: Picco, Eduardo. Universidad Tecnológica Nacional . Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.
Peer Reviewed
Materia
Acetylation
Organic synthesis
Nucleophilic
Nivel de accesibilidad
acceso abierto
Condiciones de uso
2024-07-22T22:37:18Z
Repositorio
Repositorio Institucional Abierto (UTN)
Institución
Universidad Tecnológica Nacional
OAI Identificador
oai:ria.utn.edu.ar:20.500.12272/11141
Acceder
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network_acronym_str RIAUTN
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network_name_str Repositorio Institucional Abierto (UTN)
spelling Theoretical study of acid acetylation of anilineCaglieri, SilvanaServetti, Gustavo IvánPicco, EduardoAcetylationOrganic synthesisNucleophilicThe 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 aniline 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 6-31G* basis set. Energies of all reagents and products and the energy of activation for the reaction were calculated using the MP2- 2nd order Mo/ller–Plesset method. Following the same procedure it was identified the geometric parameters and energy of intermediate. Figure 1 show the optimized structure of the intermediate and the Table 1 lists the geometric parameters, lengths and binding angles values, obtained. The calculations show 18.37 kcal/mol of activation energy.Fil: Caglieri, Silvana. Universidad Tecnológica Nacional . Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.Fil: Servetti, Gustavo Iván. Universidad Tecnológica Nacional . Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.Fil: Picco, Eduardo. Universidad Tecnológica Nacional . Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.Peer Reviewed2024-07-22T22:37:18Z2024-07-22T22:37:18Z2014info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articulopdfapplication/pdfInternational Conference on Pure and Applied Chemistry .2014http://hdl.handle.net/20.500.12272/11141-enginfo:eu-repo/semantics/openAccess2024-07-22T22:37:18Zhttp://creativecommons.org/licenses/by-nc-nd/4.0/Attribution-NonCommercial-NoDerivatives 4.0 InternacionalCaglieri , Silvana; Servetti, Gustavo Ivàn; Picco, Eduardohttps://creativecommons.org/licenses/by-nc-sa/4.0/reponame:Repositorio Institucional Abierto (UTN)instname:Universidad Tecnológica Nacional2026-09-24T12:46:23Zoai:ria.utn.edu.ar:20.500.12272/11141instacron: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 12:46:24.875Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacionalfalse
dc.title.none.fl_str_mv Theoretical study of acid acetylation of aniline
title Theoretical study of acid acetylation of aniline
spellingShingle Theoretical study of acid acetylation of aniline
Caglieri, Silvana
Acetylation
Organic synthesis
Nucleophilic
title_short Theoretical study of acid acetylation of aniline
title_full Theoretical study of acid acetylation of aniline
title_fullStr Theoretical study of acid acetylation of aniline
title_full_unstemmed Theoretical study of acid acetylation of aniline
title_sort Theoretical study of acid acetylation of aniline
dc.creator.none.fl_str_mv Caglieri, Silvana
Servetti, Gustavo Iván
Picco, Eduardo
author Caglieri, Silvana
author_facet Caglieri, Silvana
Servetti, Gustavo Iván
Picco, Eduardo
author_role author
author2 Servetti, Gustavo Iván
Picco, Eduardo
author2_role author
author
dc.subject.none.fl_str_mv Acetylation
Organic synthesis
Nucleophilic
topic Acetylation
Organic synthesis
Nucleophilic
dc.description.none.fl_txt_mv 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 aniline 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 6-31G* basis set. Energies of all reagents and products and the energy of activation for the reaction were calculated using the MP2- 2nd order Mo/ller–Plesset method. Following the same procedure it was identified the geometric parameters and energy of intermediate. Figure 1 show the optimized structure of the intermediate and the Table 1 lists the geometric parameters, lengths and binding angles values, obtained. The calculations show 18.37 kcal/mol of activation energy.
Fil: Caglieri, Silvana. Universidad Tecnológica Nacional . Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.
Fil: Servetti, Gustavo Iván. Universidad Tecnológica Nacional . Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.
Fil: Picco, Eduardo. Universidad Tecnológica Nacional . Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina.
Peer Reviewed
description 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 aniline 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 6-31G* basis set. Energies of all reagents and products and the energy of activation for the reaction were calculated using the MP2- 2nd order Mo/ller–Plesset method. Following the same procedure it was identified the geometric parameters and energy of intermediate. Figure 1 show the optimized structure of the intermediate and the Table 1 lists the geometric parameters, lengths and binding angles values, obtained. The calculations show 18.37 kcal/mol of activation energy.
publishDate 2014
dc.date.none.fl_str_mv 2014
2024-07-22T22:37:18Z
2024-07-22T22:37:18Z
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 Conference on Pure and Applied Chemistry .2014
http://hdl.handle.net/20.500.12272/11141
-
identifier_str_mv International Conference on Pure and Applied Chemistry .2014
-
url http://hdl.handle.net/20.500.12272/11141
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
2024-07-22T22:37:18Z
http://creativecommons.org/licenses/by-nc-nd/4.0/
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
Caglieri , Silvana; Servetti, Gustavo Ivàn; Picco, Eduardo
https://creativecommons.org/licenses/by-nc-sa/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv 2024-07-22T22:37:18Z
http://creativecommons.org/licenses/by-nc-nd/4.0/
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
Caglieri , Silvana; Servetti, Gustavo Ivàn; Picco, Eduardo
https://creativecommons.org/licenses/by-nc-sa/4.0/
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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
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