Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway
- Autores
- Allegretti, Patricia Ercilia; Bravo, Rodolfo Daniel; Furlong, Jorge Javier Pedro
- Año de publicación
- 2002
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- Aromatic hydrocarbons are susceptible to direct acylation by benzoic acids with high yields bearing ortho or para alkyl groups as substituents under Friedel–Crafts reaction conditions. The α-H of the alkyl moiety seems to be responsible for the observed relatively high reaction rates of conversion. Carbanion-like species are proposed as reaction intermediates, which also operate as strong bases in the reaction rate-determining steps. Trapping experiments, deuterium isotopic effects, and kinetics data favor a concerted reaction pathway where proton transfer from the hydrocarbon molecule to a carbanionic intermediate takes place with a simultaneous electrophilic attack of the carbonylic carbon atom.
Facultad de Ciencias Exactas
Laboratorio de Estudio de Compuestos Orgánicos - Materia
-
Ciencias Exactas
Química
Deuterium
Aromatic Hydrocarbon
Benzoic Acid
Proton Transfer
Reaction Pathway - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- http://creativecommons.org/licenses/by-nc-sa/4.0/
- Repositorio
.jpg)
- Institución
- Universidad Nacional de La Plata
- OAI Identificador
- oai:sedici.unlp.edu.ar:10915/132695
Ver los metadatos del registro completo
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Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction PathwayAllegretti, Patricia ErciliaBravo, Rodolfo DanielFurlong, Jorge Javier PedroCiencias ExactasQuímicaDeuteriumAromatic HydrocarbonBenzoic AcidProton TransferReaction PathwayAromatic hydrocarbons are susceptible to direct acylation by benzoic acids with high yields bearing ortho or para alkyl groups as substituents under Friedel–Crafts reaction conditions. The α-H of the alkyl moiety seems to be responsible for the observed relatively high reaction rates of conversion. Carbanion-like species are proposed as reaction intermediates, which also operate as strong bases in the reaction rate-determining steps. Trapping experiments, deuterium isotopic effects, and kinetics data favor a concerted reaction pathway where proton transfer from the hydrocarbon molecule to a carbanionic intermediate takes place with a simultaneous electrophilic attack of the carbonylic carbon atom.Facultad de Ciencias ExactasLaboratorio de Estudio de Compuestos Orgánicos2002-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf764-773http://sedici.unlp.edu.ar/handle/10915/132695enginfo:eu-repo/semantics/altIdentifier/issn/0023-1584info:eu-repo/semantics/altIdentifier/issn/1608-3210info:eu-repo/semantics/altIdentifier/doi/10.1023/a:1021626301812info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-sa/4.0/Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:32:02Zoai:sedici.unlp.edu.ar:10915/132695Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:32:03.27SEDICI (UNLP) - Universidad Nacional de La Platafalse |
| dc.title.none.fl_str_mv |
Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway |
| title |
Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway |
| spellingShingle |
Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway Allegretti, Patricia Ercilia Ciencias Exactas Química Deuterium Aromatic Hydrocarbon Benzoic Acid Proton Transfer Reaction Pathway |
| title_short |
Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway |
| title_full |
Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway |
| title_fullStr |
Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway |
| title_full_unstemmed |
Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway |
| title_sort |
Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway |
| dc.creator.none.fl_str_mv |
Allegretti, Patricia Ercilia Bravo, Rodolfo Daniel Furlong, Jorge Javier Pedro |
| author |
Allegretti, Patricia Ercilia |
| author_facet |
Allegretti, Patricia Ercilia Bravo, Rodolfo Daniel Furlong, Jorge Javier Pedro |
| author_role |
author |
| author2 |
Bravo, Rodolfo Daniel Furlong, Jorge Javier Pedro |
| author2_role |
author author |
| dc.subject.none.fl_str_mv |
Ciencias Exactas Química Deuterium Aromatic Hydrocarbon Benzoic Acid Proton Transfer Reaction Pathway |
| topic |
Ciencias Exactas Química Deuterium Aromatic Hydrocarbon Benzoic Acid Proton Transfer Reaction Pathway |
| dc.description.none.fl_txt_mv |
Aromatic hydrocarbons are susceptible to direct acylation by benzoic acids with high yields bearing ortho or para alkyl groups as substituents under Friedel–Crafts reaction conditions. The α-H of the alkyl moiety seems to be responsible for the observed relatively high reaction rates of conversion. Carbanion-like species are proposed as reaction intermediates, which also operate as strong bases in the reaction rate-determining steps. Trapping experiments, deuterium isotopic effects, and kinetics data favor a concerted reaction pathway where proton transfer from the hydrocarbon molecule to a carbanionic intermediate takes place with a simultaneous electrophilic attack of the carbonylic carbon atom. Facultad de Ciencias Exactas Laboratorio de Estudio de Compuestos Orgánicos |
| description |
Aromatic hydrocarbons are susceptible to direct acylation by benzoic acids with high yields bearing ortho or para alkyl groups as substituents under Friedel–Crafts reaction conditions. The α-H of the alkyl moiety seems to be responsible for the observed relatively high reaction rates of conversion. Carbanion-like species are proposed as reaction intermediates, which also operate as strong bases in the reaction rate-determining steps. Trapping experiments, deuterium isotopic effects, and kinetics data favor a concerted reaction pathway where proton transfer from the hydrocarbon molecule to a carbanionic intermediate takes place with a simultaneous electrophilic attack of the carbonylic carbon atom. |
| publishDate |
2002 |
| dc.date.none.fl_str_mv |
2002-11 |
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info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Articulo http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
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article |
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publishedVersion |
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http://sedici.unlp.edu.ar/handle/10915/132695 |
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eng |
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eng |
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info:eu-repo/semantics/altIdentifier/issn/0023-1584 info:eu-repo/semantics/altIdentifier/issn/1608-3210 info:eu-repo/semantics/altIdentifier/doi/10.1023/a:1021626301812 |
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