Theoretical study of acetylation of ethylamine catalyzed by Zn2+ions

A theoretical study of acetylation of ethylamine catalyzed by Zn2+ 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 o...

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Autores principales: Caglieri, Silvana, Macaño, Hèctor Rubèn
Formato: Artículo publisherVersion
Lenguaje:Inglés
Publicado: 2024
Materias:
Acetylation of ethylamine
Organic synthesis
Nucleophilic substitution
Acceso en línea:http://hdl.handle.net/20.500.12272/11182
Aporte de:
RIA - Repositorio Institucional Abierto (UTN) de Universidad Tecnológica Nacional
id I68-R174-20.500.12272-11182
record_format dspace
spelling I68-R174-20.500.12272-111822024-07-29T20:15:26Z Theoretical study of acetylation of ethylamine catalyzed by Zn2+ions Caglieri, Silvana Macaño, Hèctor Rubèn Acetylation of ethylamine Organic synthesis Nucleophilic substitution A theoretical study of acetylation of ethylamine catalyzed by Zn2+ 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 Zn2+ 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 57.82 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 9.59 kcal/mol. 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. Peer Reviewed 2024-07-29T20:15:26Z 2024-07-29T20:15:26Z 2015 info:eu-repo/semantics/article publisherVersion 18th International Symposium on Organometallic Chemistry Directed Towards Organic-Synthesis.2015 http://hdl.handle.net/20.500.12272/11182 - eng openAccess http://creativecommons.org/licenses/by-nc-nd/4.0/ Attribution-NonCommercial-NoDerivatives 4.0 Internacional Caglieri , Silvana; Macaño, Hèctor Rubèn 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 ethylamine
Organic synthesis
Nucleophilic substitution
spellingShingle Acetylation of ethylamine
Organic synthesis
Nucleophilic substitution
Caglieri, Silvana
Macaño, Hèctor Rubèn
Theoretical study of acetylation of ethylamine catalyzed by Zn2+ions
topic_facet Acetylation of ethylamine
Organic synthesis
Nucleophilic substitution
description A theoretical study of acetylation of ethylamine catalyzed by Zn2+ 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 Zn2+ 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 57.82 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 9.59 kcal/mol.
format Artículo
publisherVersion
author Caglieri, Silvana
Macaño, Hèctor Rubèn
author_facet Caglieri, Silvana
Macaño, Hèctor Rubèn
author_sort Caglieri, Silvana
title Theoretical study of acetylation of ethylamine catalyzed by Zn2+ions
title_short Theoretical study of acetylation of ethylamine catalyzed by Zn2+ions
title_full Theoretical study of acetylation of ethylamine catalyzed by Zn2+ions
title_fullStr Theoretical study of acetylation of ethylamine catalyzed by Zn2+ions
title_full_unstemmed Theoretical study of acetylation of ethylamine catalyzed by Zn2+ions
title_sort theoretical study of acetylation of ethylamine catalyzed by zn2+ions
publishDate 2024
url http://hdl.handle.net/20.500.12272/11182
work_keys_str_mv AT caglierisilvana theoreticalstudyofacetylationofethylaminecatalyzedbyzn2ions
AT macanohectorruben theoreticalstudyofacetylationofethylaminecatalyzedbyzn2ions
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