Theoretical Study of Pentyl Alcohol Acetylation

Autores
Caglieri, Silvana Claudia; Macaño, Héctor; Manca, María Lorena
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión aceptada
Descripción
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. A theoretical study of acid acetylation of pentyl alcohol from the analysis of intermediate of the reaction was carried out. Geometries of all species involved in the reaction were made and identified. All of the geometry optimizations were performed and all energies were calculated using the DFT/B3LY method and was adopted the 6-31+G* basis set. Following the same procedure it was identified the geometric parameters and energy of intermediate of reaction. 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 and theoretical work agreed that this reaction takes place with the formation of a tetrahedral intermediate. The energy of activation for the reaction was 17.30 kcal/mol The reaction and the compounds studied are shown in Figure1, R: C5H11.
Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Fil: Macaño, Héctor. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Fil: Manca, María Lorena. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Peer Reviewed
Materia
Acetilation
Pentyl alcohol
DFT
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:20.500.12272/15373
Acceder
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network_acronym_str RIAUTN
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network_name_str Repositorio Institucional Abierto (UTN)
spelling Theoretical Study of Pentyl Alcohol AcetylationCaglieri, Silvana ClaudiaMacaño, HéctorManca, María LorenaAcetilationPentyl alcoholDFTThe 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. A theoretical study of acid acetylation of pentyl alcohol from the analysis of intermediate of the reaction was carried out. Geometries of all species involved in the reaction were made and identified. All of the geometry optimizations were performed and all energies were calculated using the DFT/B3LY method and was adopted the 6-31+G* basis set. Following the same procedure it was identified the geometric parameters and energy of intermediate of reaction. 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 and theoretical work agreed that this reaction takes place with the formation of a tetrahedral intermediate. The energy of activation for the reaction was 17.30 kcal/mol The reaction and the compounds studied are shown in Figure1, R: C5H11.Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.Fil: Macaño, Héctor. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.Fil: Manca, María Lorena. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.Peer ReviewedUniversidad Tecnológica Nacional Facultad Regional Córdoba.2026-08-10T20:11:59Z2018info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articulopdfapplication/pdfPhysical Chemistry & Theoretical Chemistryhttps://hdl.handle.net/20.500.12272/15373enginfo:eu-repo/semantics/openAccessAttribution-NonCommercial-NoDerivs 2.5 Argentinahttp://creativecommons.org/licenses/by-nc-nd/2.5/ar/Caglieri, Silvana Claudia; Macaño, Héctor; Manca, María Lorena.https://creativecommons.org/licenses/by-nc-nd/4.0/reponame:Repositorio Institucional Abierto (UTN)instname:Universidad Tecnológica Nacional2026-09-24T12:47:31Zoai:ria.utn.edu.ar:20.500.12272/15373instacron: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 12:47:32.763Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacionalfalse
dc.title.none.fl_str_mv Theoretical Study of Pentyl Alcohol Acetylation
title Theoretical Study of Pentyl Alcohol Acetylation
spellingShingle Theoretical Study of Pentyl Alcohol Acetylation
Caglieri, Silvana Claudia
Acetilation
Pentyl alcohol
DFT
title_short Theoretical Study of Pentyl Alcohol Acetylation
title_full Theoretical Study of Pentyl Alcohol Acetylation
title_fullStr Theoretical Study of Pentyl Alcohol Acetylation
title_full_unstemmed Theoretical Study of Pentyl Alcohol Acetylation
title_sort Theoretical Study of Pentyl Alcohol Acetylation
dc.creator.none.fl_str_mv Caglieri, Silvana Claudia
Macaño, Héctor
Manca, María Lorena
author Caglieri, Silvana Claudia
author_facet Caglieri, Silvana Claudia
Macaño, Héctor
Manca, María Lorena
author_role author
author2 Macaño, Héctor
Manca, María Lorena
author2_role author
author
dc.subject.none.fl_str_mv Acetilation
Pentyl alcohol
DFT
topic Acetilation
Pentyl alcohol
DFT
dc.description.none.fl_txt_mv 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. A theoretical study of acid acetylation of pentyl alcohol from the analysis of intermediate of the reaction was carried out. Geometries of all species involved in the reaction were made and identified. All of the geometry optimizations were performed and all energies were calculated using the DFT/B3LY method and was adopted the 6-31+G* basis set. Following the same procedure it was identified the geometric parameters and energy of intermediate of reaction. 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 and theoretical work agreed that this reaction takes place with the formation of a tetrahedral intermediate. The energy of activation for the reaction was 17.30 kcal/mol The reaction and the compounds studied are shown in Figure1, R: C5H11.
Fil: Caglieri, Silvana Claudia. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Fil: Macaño, Héctor. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Fil: Manca, María Lorena. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Química Ambiental; Argentina.
Peer Reviewed
description 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. A theoretical study of acid acetylation of pentyl alcohol from the analysis of intermediate of the reaction was carried out. Geometries of all species involved in the reaction were made and identified. All of the geometry optimizations were performed and all energies were calculated using the DFT/B3LY method and was adopted the 6-31+G* basis set. Following the same procedure it was identified the geometric parameters and energy of intermediate of reaction. 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 and theoretical work agreed that this reaction takes place with the formation of a tetrahedral intermediate. The energy of activation for the reaction was 17.30 kcal/mol The reaction and the compounds studied are shown in Figure1, R: C5H11.
publishDate 2018
dc.date.none.fl_str_mv 2018
2026-08-10T20:11:59Z
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv Physical Chemistry & Theoretical Chemistry
https://hdl.handle.net/20.500.12272/15373
identifier_str_mv Physical Chemistry & Theoretical Chemistry
url https://hdl.handle.net/20.500.12272/15373
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; Macaño, Héctor; Manca, María Lorena.
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; Macaño, Héctor; Manca, María Lorena.
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 Facultad Regional Córdoba.
publisher.none.fl_str_mv Universidad Tecnológica Nacional Facultad 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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score 13.265058

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