Electrophilic Aromatic Nitration: Understanding Its Mechanism and Substituent Effects
Theoretical calculations and gas-phase mass spectrometric studies were performed for the reaction of the naked (NO2 +) and monosolvated (CH3NO2·NO2 +) nitronium ion with several monosubstituted aromatic compounds. From these studies, we propose a general model for regioselectivity based on the singl...
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| Veröffentlicht in: | Journal of organic chemistry 2006-08, Vol.71 (16), p.6192-6203 |
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| container_issue | 16 |
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| container_title | Journal of organic chemistry |
| container_volume | 71 |
| creator | Queiroz, Jorge Freire de Carneiro, José Walkimar de M Sabino, Adão A Sparrapan, Regina Eberlin, Marcos N Esteves, Pierre M |
| description | Theoretical calculations and gas-phase mass spectrometric studies were performed for the reaction of the naked (NO2 +) and monosolvated (CH3NO2·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 +. |
| doi_str_mv | 10.1021/jo0609475 |
| format | Article |
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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. 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| subjects | Chemistry Exact sciences and technology Kinetics and mechanisms Organic chemistry Reactivity and mechanisms |
| title | Electrophilic Aromatic Nitration: Understanding Its Mechanism and Substituent Effects |
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