Theoretical Study of Acetylation of Ethanol

Autores
Caglieri, Silvana Claudia
Año de publicación
2017
Idioma
inglés
Tipo de recurso
informe técnico
Estado
versión aceptada
Descripción
Theoretical study of acetylation of ethanol from the analysis of intermediate of the reaction was carried out. The study of acetylation of alcohols 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 means for protectinghydroxyl groups in a synthetic process. Acetylation of alcohols 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 facilitates the successive attack nucleophilic of alcohol at the position to form a tetrahedral intermediate, step determinant of the rate of the reaction. Experimental investigation (Heravi et al., 2007) was carried out and theoretical works (Kruger, 2002) agreed that this reaction takes place with the formation of a tetrahedral intermediate. The reaction and the compounds studied are shown in Figure1. In the present theoretical work were investigated the structure and energy of the tetrahedral intermediate of the reaction. Geometries of all species involved in the acetylation were made and identified. All of the geometry optimizations were performed and all energies were calculated using the method at the DFT/B3LYP level of theory and the MP2 method. Was adopted the 6-31+G* basis set. Following the same procedure it was identified the geometric parameters and energy of intermediate of reaction. Figure 2 show the optimized structure of the intermediate and the Table 1 lists the geometric parameters, lengths and binding angles values, obtained. The calculations show 14.12 kcal/mol of activation energy for the reaction using the DFT/B3LYP method, which reported the lower energy values.
Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Peer Reviewed
Materia
Acetilation
Alcohols
Organic synthesis
Nivel de accesibilidad
acceso abierto
Condiciones de uso
Attribution-NonCommercial-NoDerivs 2.5 Argentina
Repositorio
Repositorio Institucional Abierto (UTN)
Institución
Universidad Tecnológica Nacional
OAI Identificador
oai:ria.utn.edu.ar:20.500.12272/15252
Acceder
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network_name_str Repositorio Institucional Abierto (UTN)
spelling Theoretical Study of Acetylation of EthanolCaglieri, Silvana ClaudiaAcetilationAlcoholsOrganic synthesisTheoretical study of acetylation of ethanol from the analysis of intermediate of the reaction was carried out. The study of acetylation of alcohols 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 means for protectinghydroxyl groups in a synthetic process. Acetylation of alcohols 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 facilitates the successive attack nucleophilic of alcohol at the position to form a tetrahedral intermediate, step determinant of the rate of the reaction. Experimental investigation (Heravi et al., 2007) was carried out and theoretical works (Kruger, 2002) agreed that this reaction takes place with the formation of a tetrahedral intermediate. The reaction and the compounds studied are shown in Figure1. In the present theoretical work were investigated the structure and energy of the tetrahedral intermediate of the reaction. Geometries of all species involved in the acetylation were made and identified. All of the geometry optimizations were performed and all energies were calculated using the method at the DFT/B3LYP level of theory and the MP2 method. Was adopted the 6-31+G* basis set. Following the same procedure it was identified the geometric parameters and energy of intermediate of reaction. Figure 2 show the optimized structure of the intermediate and the Table 1 lists the geometric parameters, lengths and binding angles values, obtained. The calculations show 14.12 kcal/mol of activation energy for the reaction using the DFT/B3LYP method, which reported the lower energy values.Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.Peer ReviewedInformación Tecnológica2026-07-01T20:18:31Z2017info:eu-repo/semantics/reportinfo:eu-repo/semantics/acceptedVersionhttp://purl.org/coar/resource_type/c_18ghinfo:ar-repo/semantics/informeTecnicopdfapplication/pdfhttps://hdl.handle.net/20.500.12272/15252enginfo:eu-repo/semantics/openAccessAttribution-NonCommercial-NoDerivs 2.5 Argentinahttp://creativecommons.org/licenses/by-nc-nd/2.5/ar/Caglieri, Silvana Claudia.https://creativecommons.org/licenses/by-nc-nd/4.0/reponame:Repositorio Institucional Abierto (UTN)instname:Universidad Tecnológica Nacional2026-09-24T12:48:57Zoai:ria.utn.edu.ar:20.500.12272/15252instacron: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 12:48:58.467Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacionalfalse
dc.title.none.fl_str_mv Theoretical Study of Acetylation of Ethanol
title Theoretical Study of Acetylation of Ethanol
spellingShingle Theoretical Study of Acetylation of Ethanol
Caglieri, Silvana Claudia
Acetilation
Alcohols
Organic synthesis
title_short Theoretical Study of Acetylation of Ethanol
title_full Theoretical Study of Acetylation of Ethanol
title_fullStr Theoretical Study of Acetylation of Ethanol
title_full_unstemmed Theoretical Study of Acetylation of Ethanol
title_sort Theoretical Study of Acetylation of Ethanol
dc.creator.none.fl_str_mv Caglieri, Silvana Claudia
author Caglieri, Silvana Claudia
author_facet Caglieri, Silvana Claudia
author_role author
dc.subject.none.fl_str_mv Acetilation
Alcohols
Organic synthesis
topic Acetilation
Alcohols
Organic synthesis
dc.description.none.fl_txt_mv Theoretical study of acetylation of ethanol from the analysis of intermediate of the reaction was carried out. The study of acetylation of alcohols 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 means for protectinghydroxyl groups in a synthetic process. Acetylation of alcohols 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 facilitates the successive attack nucleophilic of alcohol at the position to form a tetrahedral intermediate, step determinant of the rate of the reaction. Experimental investigation (Heravi et al., 2007) was carried out and theoretical works (Kruger, 2002) agreed that this reaction takes place with the formation of a tetrahedral intermediate. The reaction and the compounds studied are shown in Figure1. In the present theoretical work were investigated the structure and energy of the tetrahedral intermediate of the reaction. Geometries of all species involved in the acetylation were made and identified. All of the geometry optimizations were performed and all energies were calculated using the method at the DFT/B3LYP level of theory and the MP2 method. Was adopted the 6-31+G* basis set. Following the same procedure it was identified the geometric parameters and energy of intermediate of reaction. Figure 2 show the optimized structure of the intermediate and the Table 1 lists the geometric parameters, lengths and binding angles values, obtained. The calculations show 14.12 kcal/mol of activation energy for the reaction using the DFT/B3LYP method, which reported the lower energy values.
Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Peer Reviewed
description Theoretical study of acetylation of ethanol from the analysis of intermediate of the reaction was carried out. The study of acetylation of alcohols 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 means for protectinghydroxyl groups in a synthetic process. Acetylation of alcohols 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 facilitates the successive attack nucleophilic of alcohol at the position to form a tetrahedral intermediate, step determinant of the rate of the reaction. Experimental investigation (Heravi et al., 2007) was carried out and theoretical works (Kruger, 2002) agreed that this reaction takes place with the formation of a tetrahedral intermediate. The reaction and the compounds studied are shown in Figure1. In the present theoretical work were investigated the structure and energy of the tetrahedral intermediate of the reaction. Geometries of all species involved in the acetylation were made and identified. All of the geometry optimizations were performed and all energies were calculated using the method at the DFT/B3LYP level of theory and the MP2 method. Was adopted the 6-31+G* basis set. Following the same procedure it was identified the geometric parameters and energy of intermediate of reaction. Figure 2 show the optimized structure of the intermediate and the Table 1 lists the geometric parameters, lengths and binding angles values, obtained. The calculations show 14.12 kcal/mol of activation energy for the reaction using the DFT/B3LYP method, which reported the lower energy values.
publishDate 2017
dc.date.none.fl_str_mv 2017
2026-07-01T20:18:31Z
dc.type.none.fl_str_mv info:eu-repo/semantics/report
info:eu-repo/semantics/acceptedVersion
http://purl.org/coar/resource_type/c_18gh
info:ar-repo/semantics/informeTecnico
format report
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.12272/15252
url https://hdl.handle.net/20.500.12272/15252
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
Attribution-NonCommercial-NoDerivs 2.5 Argentina
http://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Caglieri, Silvana Claudia.
https://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivs 2.5 Argentina
http://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Caglieri, Silvana Claudia.
https://creativecommons.org/licenses/by-nc-nd/4.0/
dc.format.none.fl_str_mv pdf
application/pdf
dc.publisher.none.fl_str_mv Información Tecnológica
publisher.none.fl_str_mv Información Tecnológica
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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