Theoretical study of aniline acetylation catalyzed by Mn2+ ions
Theoretical study of aniline acetylation catalyzed by Mn2+ ions from the analysis of intermediate of the reaction was carried out. The study of acetylation of amines is of great interest by the utility of its products of reaction and is one of the most frequently used transformations in organic s...
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| Formato: | Artículo publisherVersion |
| Lenguaje: | Inglés |
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2024
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| Acceso en línea: | http://hdl.handle.net/20.500.12272/11197 |
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I68-R174-20.500.12272-11197 |
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I68-R174-20.500.12272-111972024-07-30T19:24:26Z Theoretical study of aniline acetylation catalyzed by Mn2+ ions Caglieri, Silvana Aniline acetylation Organic synthesis Synthetic process Theoretical study of aniline acetylation catalyzed by Mn2+ ions from the analysis of intermediate of the reaction was carried out. The study of acetylation of amines 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 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 Lewis acid1 , metallic ion. In reaction mechanism, the metallic ion formed a complex with the oxygen of the acetic anhydride carbonyl, facilitating the polarization of the same and the successive addition of amine at the position to form a tetrahedral intermediate, determining step of the rate of the reaction. Experimental work2 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 catalyzed by Mn2+ ions. 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/B3LYP level of theory and the method MP2. Were adopted the 6-31+G* basis sets. Energies were calculated using the Mechanics-UFF method. Following the same procedure it was identified the geometric parameters and energy of reaction intermediate. The calculations show 77.38 kcal/mol of energy for the tetrahedral intermediate and the energy of activation for the reaction was 23.22 kcal/mol. Fil: Caglieri, Silvana. Universidad Tecnológica Nacional. Facultad Regional Córdoba. Centro de Investigación y Transferencia en Ingeniería Química Ambiental; Argentina. Peer Reviewed 2024-07-30T19:24:26Z 2024-07-30T19:24:26Z 2015 info:eu-repo/semantics/article publisherVersion 5th Simposio Latinoamericano de Química de Coordinación y Organometálica.2015 http://hdl.handle.net/20.500.12272/11197 - 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 |
Aniline acetylation Organic synthesis Synthetic process |
| spellingShingle |
Aniline acetylation Organic synthesis Synthetic process Caglieri, Silvana Theoretical study of aniline acetylation catalyzed by Mn2+ ions |
| topic_facet |
Aniline acetylation Organic synthesis Synthetic process |
| description |
Theoretical study of aniline acetylation catalyzed by Mn2+ ions from the analysis of
intermediate of the reaction was carried out. The study of acetylation of amines 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 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
Lewis acid1
, metallic ion. In reaction mechanism, the metallic ion formed a complex with the
oxygen of the acetic anhydride carbonyl, facilitating the polarization of the same and the
successive addition of amine at the position to form a tetrahedral intermediate, determining step
of the rate of the reaction. Experimental work2
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 catalyzed by Mn2+ ions.
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/B3LYP level of theory and
the method MP2. Were adopted the 6-31+G* basis sets. Energies were calculated using the
Mechanics-UFF method. Following the same procedure it was identified the geometric
parameters and energy of reaction intermediate.
The calculations show 77.38 kcal/mol of energy for the tetrahedral intermediate and the
energy of activation for the reaction was 23.22 kcal/mol. |
| format |
Artículo publisherVersion |
| author |
Caglieri, Silvana |
| author_facet |
Caglieri, Silvana |
| author_sort |
Caglieri, Silvana |
| title |
Theoretical study of aniline acetylation catalyzed by Mn2+ ions |
| title_short |
Theoretical study of aniline acetylation catalyzed by Mn2+ ions |
| title_full |
Theoretical study of aniline acetylation catalyzed by Mn2+ ions |
| title_fullStr |
Theoretical study of aniline acetylation catalyzed by Mn2+ ions |
| title_full_unstemmed |
Theoretical study of aniline acetylation catalyzed by Mn2+ ions |
| title_sort |
theoretical study of aniline acetylation catalyzed by mn2+ ions |
| publishDate |
2024 |
| url |
http://hdl.handle.net/20.500.12272/11197 |
| work_keys_str_mv |
AT caglierisilvana theoreticalstudyofanilineacetylationcatalyzedbymn2ions |
| _version_ |
1809230377223454720 |