Theoretical study of acetylation of methanol

Autores
Caglieri, Silvana Claudia
Año de publicación
2017
Idioma
inglés
Tipo de recurso
informe técnico
Estado
versión publicada
Descripción
Theoretical study of acetylation of methanol 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 protecting hydroxyl 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 and theoretical works agreed that this reaction takes place with the formation of a tetrahedral intermediate. 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 reaction intermediate. The calculations show 13.68 kcal/mol of activation energy for the reaction using the DFT 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.
Materia
alcohols
DFT
esters
MP2
Nivel de accesibilidad
acceso abierto
Condiciones de uso
Attribution-NonCommercial-NoDerivatives 4.0 International
Repositorio
Repositorio Institucional Abierto (UTN)
Institución
Universidad Tecnológica Nacional
OAI Identificador
oai:ria.utn.edu.ar:20.500.12272/14807
Acceder
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network_acronym_str RIAUTN
repository_id_str a
network_name_str Repositorio Institucional Abierto (UTN)
spelling Theoretical study of acetylation of methanolCaglieri, Silvana ClaudiaalcoholsDFTestersMP2Theoretical study of acetylation of methanol 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 protecting hydroxyl 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 and theoretical works agreed that this reaction takes place with the formation of a tetrahedral intermediate. 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 reaction intermediate. The calculations show 13.68 kcal/mol of activation energy for the reaction using the DFT method, which reported the lower energy valuesFil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.UTN- FRC2026-03-13T20:17:58Z2017info:eu-repo/semantics/reportinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_18ghinfo:ar-repo/semantics/informeTecnicopdfapplication/pdfhttps://hdl.handle.net/20.500.12272/14807enginfo:eu-repo/semantics/openAccessAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/Silvana Caglierireponame:Repositorio Institucional Abierto (UTN)instname:Universidad Tecnológica Nacional2026-09-24T12:46:54Zoai:ria.utn.edu.ar:20.500.12272/14807instacron: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 12:46:55.091Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacionalfalse
dc.title.none.fl_str_mv Theoretical study of acetylation of methanol
title Theoretical study of acetylation of methanol
spellingShingle Theoretical study of acetylation of methanol
Caglieri, Silvana Claudia
alcohols
DFT
esters
MP2
title_short Theoretical study of acetylation of methanol
title_full Theoretical study of acetylation of methanol
title_fullStr Theoretical study of acetylation of methanol
title_full_unstemmed Theoretical study of acetylation of methanol
title_sort Theoretical study of acetylation of methanol
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 alcohols
DFT
esters
MP2
topic alcohols
DFT
esters
MP2
dc.description.none.fl_txt_mv Theoretical study of acetylation of methanol 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 protecting hydroxyl 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 and theoretical works agreed that this reaction takes place with the formation of a tetrahedral intermediate. 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 reaction intermediate. The calculations show 13.68 kcal/mol of activation energy for the reaction using the DFT 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.
description Theoretical study of acetylation of methanol 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 protecting hydroxyl 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 and theoretical works agreed that this reaction takes place with the formation of a tetrahedral intermediate. 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 reaction intermediate. The calculations show 13.68 kcal/mol of activation energy for the reaction using the DFT method, which reported the lower energy values
publishDate 2017
dc.date.none.fl_str_mv 2017
2026-03-13T20:17:58Z
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/20.500.12272/14807
url https://hdl.handle.net/20.500.12272/14807
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
Silvana Caglieri
eu_rights_str_mv openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
Silvana Caglieri
dc.format.none.fl_str_mv pdf
application/pdf
dc.publisher.none.fl_str_mv UTN- FRC
publisher.none.fl_str_mv UTN- FRC
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
_version_ 1877230930574180352
score 13.24418

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