Theoretical study of alkaline acetylation of diphenylamine

Autores
Caglieri, Silvana; Macaño, Hèctor Rubèn; Servetti, Gustavo Iván
Año de publicación
2016
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 and the amide bond is found to be present in a large number of pharmacologically active molecules. Acetylation of amine is a nucleophilic substitution reaction. This reaction is carried out with acetic anhydride in the presence of amine bases such as tertiary amine and pyridine. Computational investigation1 and an experimental work2 , agreed that this reaction takes place with the formation of a tetrahedral intermediate. A theoretical study of alkaline acetylation of diphenylamine from the analysis of intermediate of the reaction was carried out. Geometries of all species involved in the acetylation were made and identified. Energies of all reagents and products and the energy of activation for the reaction were calculated using the method DFT - Density Functional Theory with B3LYP level of theory and was adopted the 6-31+G* basis set. 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 18.01 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: Macaño, Hèctor Rubèn. 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 amines
Acetic anhydride
Tertiary amine
Piridine
Nivel de accesibilidad
acceso abierto
Condiciones de uso
2024-08-07T21:08:40Z
Repositorio
Repositorio Institucional Abierto (UTN)
Institución
Universidad Tecnológica Nacional
OAI Identificador
oai:ria.utn.edu.ar:20.500.12272/11264
Acceder
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network_acronym_str RIAUTN
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network_name_str Repositorio Institucional Abierto (UTN)
spelling Theoretical study of alkaline acetylation of diphenylamineCaglieri, SilvanaMacaño, Hèctor RubènServetti, Gustavo IvánAcetylation of aminesAcetic anhydrideTertiary aminePiridineThe 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 and the amide bond is found to be present in a large number of pharmacologically active molecules. Acetylation of amine is a nucleophilic substitution reaction. This reaction is carried out with acetic anhydride in the presence of amine bases such as tertiary amine and pyridine. Computational investigation1 and an experimental work2 , agreed that this reaction takes place with the formation of a tetrahedral intermediate. A theoretical study of alkaline acetylation of diphenylamine from the analysis of intermediate of the reaction was carried out. Geometries of all species involved in the acetylation were made and identified. Energies of all reagents and products and the energy of activation for the reaction were calculated using the method DFT - Density Functional Theory with B3LYP level of theory and was adopted the 6-31+G* basis set. 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 18.01 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: Macaño, Hèctor Rubèn. 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 Reviewed2024-08-07T21:08:40Z2024-08-07T21:08:40Z2016info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articulopdfapplication/pdfPure and Applied Chemistry International Conference.2016http://hdl.handle.net/20.500.12272/11264-enginfo:eu-repo/semantics/openAccess2024-08-07T21:08:40Zhttp://creativecommons.org/licenses/by-nc-nd/4.0/Attribution-NonCommercial-NoDerivatives 4.0 InternacionalCaglieri, Silvana; Macaño, Hèctor Rubèn; Servetti, Gustavo Ivànhttps://creativecommons.org/licenses/by-nc-sa/4.0/reponame:Repositorio Institucional Abierto (UTN)instname:Universidad Tecnológica Nacional2026-10-01T11:57:07Zoai:ria.utn.edu.ar:20.500.12272/11264instacron: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 11:57:08.238Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacionalfalse
dc.title.none.fl_str_mv Theoretical study of alkaline acetylation of diphenylamine
title Theoretical study of alkaline acetylation of diphenylamine
spellingShingle Theoretical study of alkaline acetylation of diphenylamine
Caglieri, Silvana
Acetylation of amines
Acetic anhydride
Tertiary amine
Piridine
title_short Theoretical study of alkaline acetylation of diphenylamine
title_full Theoretical study of alkaline acetylation of diphenylamine
title_fullStr Theoretical study of alkaline acetylation of diphenylamine
title_full_unstemmed Theoretical study of alkaline acetylation of diphenylamine
title_sort Theoretical study of alkaline acetylation of diphenylamine
dc.creator.none.fl_str_mv Caglieri, Silvana
Macaño, Hèctor Rubèn
Servetti, Gustavo Iván
author Caglieri, Silvana
author_facet Caglieri, Silvana
Macaño, Hèctor Rubèn
Servetti, Gustavo Iván
author_role author
author2 Macaño, Hèctor Rubèn
Servetti, Gustavo Iván
author2_role author
author
dc.subject.none.fl_str_mv Acetylation of amines
Acetic anhydride
Tertiary amine
Piridine
topic Acetylation of amines
Acetic anhydride
Tertiary amine
Piridine
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 and the amide bond is found to be present in a large number of pharmacologically active molecules. Acetylation of amine is a nucleophilic substitution reaction. This reaction is carried out with acetic anhydride in the presence of amine bases such as tertiary amine and pyridine. Computational investigation1 and an experimental work2 , agreed that this reaction takes place with the formation of a tetrahedral intermediate. A theoretical study of alkaline acetylation of diphenylamine from the analysis of intermediate of the reaction was carried out. Geometries of all species involved in the acetylation were made and identified. Energies of all reagents and products and the energy of activation for the reaction were calculated using the method DFT - Density Functional Theory with B3LYP level of theory and was adopted the 6-31+G* basis set. 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 18.01 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: Macaño, Hèctor Rubèn. 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 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 and the amide bond is found to be present in a large number of pharmacologically active molecules. Acetylation of amine is a nucleophilic substitution reaction. This reaction is carried out with acetic anhydride in the presence of amine bases such as tertiary amine and pyridine. Computational investigation1 and an experimental work2 , agreed that this reaction takes place with the formation of a tetrahedral intermediate. A theoretical study of alkaline acetylation of diphenylamine from the analysis of intermediate of the reaction was carried out. Geometries of all species involved in the acetylation were made and identified. Energies of all reagents and products and the energy of activation for the reaction were calculated using the method DFT - Density Functional Theory with B3LYP level of theory and was adopted the 6-31+G* basis set. 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 18.01 kcal/mol of activation energy.
publishDate 2016
dc.date.none.fl_str_mv 2016
2024-08-07T21:08:40Z
2024-08-07T21:08:40Z
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 Pure and Applied Chemistry International Conference.2016
http://hdl.handle.net/20.500.12272/11264
-
identifier_str_mv Pure and Applied Chemistry International Conference.2016
-
url http://hdl.handle.net/20.500.12272/11264
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
2024-08-07T21:08:40Z
http://creativecommons.org/licenses/by-nc-nd/4.0/
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
Caglieri, Silvana; Macaño, Hèctor Rubèn; Servetti, Gustavo Ivàn
https://creativecommons.org/licenses/by-nc-sa/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv 2024-08-07T21:08:40Z
http://creativecommons.org/licenses/by-nc-nd/4.0/
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
Caglieri, Silvana; Macaño, Hèctor Rubèn; 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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score 13.365483

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