Theoretical study of acid acetylation of ethylamine

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 reactio...

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Autor principal: Caglieri, Silvana
Formato: Artículo publisherVersion
Lenguaje:Inglés
Publicado: 2024
Materias:
Acetylation
Ethylamine
AM1
DFT
Acceso en línea:http://hdl.handle.net/20.500.12272/11153
Aporte de:
RIA - Repositorio Institucional Abierto (UTN) de Universidad Tecnológica Nacional
id I68-R174-20.500.12272-11153
record_format dspace
spelling I68-R174-20.500.12272-111532024-07-23T20:35:54Z Theoretical study of acid acetylation of ethylamine Caglieri, Silvana Acetylation Ethylamine AM1 DFT 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 2024-07-23T20:35:54Z 2024-07-23T20:35:54Z 2014 info:eu-repo/semantics/article publisherVersion XL Congreso de Quìmicos Teòricos de Expresiòn Latina.2014 http://hdl.handle.net/20.500.12272/11153 - eng openAccess 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/ pdf
institution Universidad Tecnológica Nacional
institution_str I-68
repository_str R-174
collection RIA - Repositorio Institucional Abierto (UTN)
language Inglés
topic Acetylation
Ethylamine
AM1
DFT
spellingShingle Acetylation
Ethylamine
AM1
DFT
Caglieri, Silvana
Theoretical study of acid acetylation of ethylamine
topic_facet Acetylation
Ethylamine
AM1
DFT
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.
format Artículo
publisherVersion
author Caglieri, Silvana
author_facet Caglieri, Silvana
author_sort Caglieri, Silvana
title Theoretical study of acid acetylation of ethylamine
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
publishDate 2024
url http://hdl.handle.net/20.500.12272/11153
work_keys_str_mv AT caglierisilvana theoreticalstudyofacidacetylationofethylamine
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