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Type: Artigo de periódico
Title: Electrophilic aromatic nitration: Understanding its mechanism and substituent effects
Author: de Queiroz, JF
Carneiro, JWD
Sabino, AA
Sparrapan, R
Eberlin, MN
Esteves, PM
Abstract: Theoretical calculations and gas-phase mass spectrometric studies were performed for the reaction of the naked (NO2+) and monosolvated (CH3NO2 center dot NO2+) nitronium ion with several monosubstituted aromatic compounds. From these studies, we propose a general model for regioselectivity based on the single-electron transfer (SET) mechanism and an alternative mechanistic scheme for electrophilic aromatic nitration. This scheme considers the SET and the polar (Ingold-Hughes) mechanisms as extremes in a continuum pathway, the occurrence and extents of both mechanisms being governed mainly by the ability, or lack of ability, of the aromatic compound to transfer an electron to NO2+.
Country: EUA
Editor: Amer Chemical Soc
Citation: Journal Of Organic Chemistry. Amer Chemical Soc, v. 71, n. 16, n. 6192, n. 6203, 2006.
Rights: fechado
Identifier DOI: 10.1021/jo0609475
Date Issue: 2006
Appears in Collections:Unicamp - Artigos e Outros Documentos

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