Theoretical study of isopropyl alcohol acetilation

Autores
Caglieri, Silvana Claudia; Dalmasso, Pablo Roberto
Año de publicación
2017
Idioma
inglés
Tipo de recurso
informe técnico
Estado
versión publicada
Descripción
Theoretical study of isopropyl alcohol acetylation 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 isone of the most frequently used transformations in organic synthesis as it provides an efficient means for protecting hydroxyl groups ina synthetic process (Petursson, 2013). 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 studies (Heravi et al., 2007), (Xie et al., 2011) and (Esmaeilpour and Sardarian, 2014) were carried out and theoretical work (Kruger, 2002) agreed that this reaction takes place with the formation of a tetrahedral intermediate. The reaction and the compounds studied are shown in.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 17.13 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.
Fil: Dalmasso, Pablo Roberto. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Peer Reviewed
Materia
Acetylation
Bronsted acid
Carbonyl carbon
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:20.500.12272/15230
Acceder
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network_acronym_str RIAUTN
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network_name_str Repositorio Institucional Abierto (UTN)
spelling Theoretical study of isopropyl alcohol acetilationCaglieri, Silvana ClaudiaDalmasso, Pablo RobertoAcetylationBronsted acidCarbonyl carbonTheoretical study of isopropyl alcohol acetylation 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 isone of the most frequently used transformations in organic synthesis as it provides an efficient means for protecting hydroxyl groups ina synthetic process (Petursson, 2013). 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 studies (Heravi et al., 2007), (Xie et al., 2011) and (Esmaeilpour and Sardarian, 2014) were carried out and theoretical work (Kruger, 2002) agreed that this reaction takes place with the formation of a tetrahedral intermediate. The reaction and the compounds studied are shown in.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 17.13 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.Fil: Dalmasso, Pablo Roberto. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.Peer ReviewedUniversidad Tecnológica Nacional Regional Córdoba.2026-06-24T20:22:58Z2017info:eu-repo/semantics/reportinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_18ghinfo:ar-repo/semantics/informeTecnicopdfapplication/pdfhttps://hdl.handle.net/20.500.12272/15230enginfo:eu-repo/semantics/openAccessAttribution-NonCommercial-NoDerivs 2.5 Argentinahttp://creativecommons.org/licenses/by-nc-nd/2.5/ar/Caglieri, Silvana Claudia; Dalmasso, Pablo Roberto.https://creativecommons.org/licenses/by-nc-nd/4.0/reponame:Repositorio Institucional Abierto (UTN)instname:Universidad Tecnológica Nacional2026-09-24T12:45:46Zoai:ria.utn.edu.ar:20.500.12272/15230instacron: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 12:45:48.239Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacionalfalse
dc.title.none.fl_str_mv Theoretical study of isopropyl alcohol acetilation
title Theoretical study of isopropyl alcohol acetilation
spellingShingle Theoretical study of isopropyl alcohol acetilation
Caglieri, Silvana Claudia
Acetylation
Bronsted acid
Carbonyl carbon
title_short Theoretical study of isopropyl alcohol acetilation
title_full Theoretical study of isopropyl alcohol acetilation
title_fullStr Theoretical study of isopropyl alcohol acetilation
title_full_unstemmed Theoretical study of isopropyl alcohol acetilation
title_sort Theoretical study of isopropyl alcohol acetilation
dc.creator.none.fl_str_mv Caglieri, Silvana Claudia
Dalmasso, Pablo Roberto
author Caglieri, Silvana Claudia
author_facet Caglieri, Silvana Claudia
Dalmasso, Pablo Roberto
author_role author
author2 Dalmasso, Pablo Roberto
author2_role author
dc.subject.none.fl_str_mv Acetylation
Bronsted acid
Carbonyl carbon
topic Acetylation
Bronsted acid
Carbonyl carbon
dc.description.none.fl_txt_mv Theoretical study of isopropyl alcohol acetylation 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 isone of the most frequently used transformations in organic synthesis as it provides an efficient means for protecting hydroxyl groups ina synthetic process (Petursson, 2013). 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 studies (Heravi et al., 2007), (Xie et al., 2011) and (Esmaeilpour and Sardarian, 2014) were carried out and theoretical work (Kruger, 2002) agreed that this reaction takes place with the formation of a tetrahedral intermediate. The reaction and the compounds studied are shown in.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 17.13 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.
Fil: Dalmasso, Pablo Roberto. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Peer Reviewed
description Theoretical study of isopropyl alcohol acetylation 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 isone of the most frequently used transformations in organic synthesis as it provides an efficient means for protecting hydroxyl groups ina synthetic process (Petursson, 2013). 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 studies (Heravi et al., 2007), (Xie et al., 2011) and (Esmaeilpour and Sardarian, 2014) were carried out and theoretical work (Kruger, 2002) agreed that this reaction takes place with the formation of a tetrahedral intermediate. The reaction and the compounds studied are shown in.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 17.13 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
2026-06-24T20:22:58Z
dc.type.none.fl_str_mv info:eu-repo/semantics/report
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_18gh
info:ar-repo/semantics/informeTecnico
format report
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.12272/15230
url https://hdl.handle.net/20.500.12272/15230
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; Dalmasso, Pablo Roberto.
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; Dalmasso, Pablo Roberto.
https://creativecommons.org/licenses/by-nc-nd/4.0/
dc.format.none.fl_str_mv pdf
application/pdf
dc.publisher.none.fl_str_mv Universidad Tecnológica Nacional Regional Córdoba.
publisher.none.fl_str_mv Universidad Tecnológica Nacional Regional Córdoba.
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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