Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway

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....

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Detalles Bibliográficos
Autores principales: Allegretti, Patricia Ercilia, Bravo, Rodolfo Daniel, Furlong, Jorge Javier Pedro
Formato: Articulo
Lenguaje:Inglés
Publicado: 2002
Materias:
Ciencias Exactas
Química
Deuterium
Aromatic Hydrocarbon
Benzoic Acid
Proton Transfer
Reaction Pathway
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/132695
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-132695
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Ciencias Exactas
Química
Deuterium
Aromatic Hydrocarbon
Benzoic Acid
Proton Transfer
Reaction Pathway
spellingShingle Ciencias Exactas
Química
Deuterium
Aromatic Hydrocarbon
Benzoic Acid
Proton Transfer
Reaction Pathway
Allegretti, Patricia Ercilia
Bravo, Rodolfo Daniel
Furlong, Jorge Javier Pedro
Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel Reaction Pathway
topic_facet Ciencias Exactas
Química
Deuterium
Aromatic Hydrocarbon
Benzoic Acid
Proton Transfer
Reaction Pathway
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.
format Articulo
Articulo
author Allegretti, Patricia Ercilia
Bravo, Rodolfo Daniel
Furlong, Jorge Javier Pedro
author_facet Allegretti, Patricia Ercilia
Bravo, Rodolfo Daniel
Furlong, Jorge Javier Pedro
author_sort Allegretti, Patricia Ercilia
title Mechanism of Aromatic Hydrocarbon Acylation by Substituted Benzoic Acids: A Novel 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
publishDate 2002
url http://sedici.unlp.edu.ar/handle/10915/132695
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AT furlongjorgejavierpedro mechanismofaromatichydrocarbonacylationbysubstitutedbenzoicacidsanovelreactionpathway
bdutipo_str Repositorios
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