Theoretical study of alkaline acetylation of diphenylamine

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...

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Autores principales: Caglieri, Silvana, Macaño, Hèctor Rubèn, Servetti, Gustavo Iván
Formato: Artículo publisherVersion
Lenguaje:Inglés
Publicado: 2024
Materias:
Acetylation of amines
Acetic anhydride
Tertiary amine
Piridine
Acceso en línea:http://hdl.handle.net/20.500.12272/11264
Aporte de:
RIA - Repositorio Institucional Abierto (UTN) de Universidad Tecnológica Nacional
id I68-R174-20.500.12272-11264
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spelling I68-R174-20.500.12272-112642024-08-07T21:08:40Z Theoretical study of alkaline acetylation of diphenylamine Caglieri, Silvana Macaño, Hèctor Rubèn Servetti, Gustavo Iván Acetylation of amines Acetic anhydride Tertiary amine Piridine 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 2024-08-07T21:08:40Z 2024-08-07T21:08:40Z 2016 info:eu-repo/semantics/article publisherVersion Pure and Applied Chemistry International Conference.2016 http://hdl.handle.net/20.500.12272/11264 - eng openAccess 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/ pdf
institution Universidad Tecnológica Nacional
institution_str I-68
repository_str R-174
collection RIA - Repositorio Institucional Abierto (UTN)
language Inglés
topic Acetylation of amines
Acetic anhydride
Tertiary amine
Piridine
spellingShingle Acetylation of amines
Acetic anhydride
Tertiary amine
Piridine
Caglieri, Silvana
Macaño, Hèctor Rubèn
Servetti, Gustavo Iván
Theoretical study of alkaline acetylation of diphenylamine
topic_facet Acetylation of amines
Acetic anhydride
Tertiary amine
Piridine
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.
format Artículo
publisherVersion
author Caglieri, Silvana
Macaño, Hèctor Rubèn
Servetti, Gustavo Iván
author_facet Caglieri, Silvana
Macaño, Hèctor Rubèn
Servetti, Gustavo Iván
author_sort Caglieri, Silvana
title Theoretical study of alkaline acetylation of diphenylamine
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
publishDate 2024
url http://hdl.handle.net/20.500.12272/11264
work_keys_str_mv AT caglierisilvana theoreticalstudyofalkalineacetylationofdiphenylamine
AT macanohectorruben theoreticalstudyofalkalineacetylationofdiphenylamine
AT servettigustavoivan theoreticalstudyofalkalineacetylationofdiphenylamine
_version_ 1809230386105942016

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