Gas-phase electrophilic aromatic substitution of electron-rich and electron-deficient aromatic compounds

1998 ◽  
pp. 2187-2194 ◽  
Author(s):  
Robert W. Holman ◽  
Todd Eary ◽  
Ed Whittle ◽  
Michael L. Gross
Keyword(s):  
Gas Phase ◽  
Aromatic Compounds ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution

The role of the lifetimes of ion–neutral complexes in gas-phase electrophilic aromatic substitution

1998 ◽  
Vol 283 (5-6) ◽  
pp. 307-312 ◽  
Author(s):  
Massimiliano Aschi ◽  
Marina Attinà ◽  
Giuseppe D'Arcangelo
Keyword(s):  
Gas Phase ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution

Complexes of copper(I) with aromatic compounds facilitate selective electrophilic aromatic substitution

2018 ◽  
Vol 71 (11-13) ◽  
pp. 1738-1748
Author(s):  
Magal Saphier ◽  
Inna Levitsky ◽  
Alexandra Masarwa ◽  
Oshra Saphier
Keyword(s):  
Aromatic Compounds ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution

Origin of the Regioselectivity in the Gas-Phase Aniline+CH3+Electrophilic Aromatic Substitution

ChemPhysChem ◽  
2015 ◽  
Vol 16 (11) ◽  
pp. 2366-2374
Author(s):  
Daniel Kinzel ◽  
Shmuel Zilberg ◽  
Leticia González
Keyword(s):  
Gas Phase ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution

Anisole nitration during gamma-irradiation of aqueous nitrite and nitrate solutions: free radical versus ionic mechanisms

2010 ◽  
Vol 7 (2) ◽  
pp. 183 ◽  
Author(s):  
Gracy Elias ◽  
Bruce J. Mincher ◽  
Stephen P. Mezyk ◽  
Thomas D. Cullen ◽  
Leigh R. Martin
Keyword(s):  
Free Radical ◽  
Water Treatment ◽  
Condensed Phase ◽  
Aromatic Compounds ◽  
Nitrous Acid ◽  
Radical Reactions ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Beam Irradiation ◽  
Free Radical Reactions

Environmental context. The nitration of aromatic compounds is an important source of toxic, carcinogenic, and mutagenic species in the atmosphere. Gas phase nitration typically occurs by free radical reactions. Condensed-phase free radical reactions may also be relevant in fog and cloud water in polluted areas, in urban aerosols with low pH, in water treatment using advanced oxidation processes such as e-beam irradiation, and in nuclear waste treatment applications. This paper discusses research towards an improved understanding of nitration of aromatic compounds in the condensed phase under conditions conducive to free radical formation. Abstract. In the irradiated, acidic condensed phase, radiation-enhanced nitrous acid-catalysed, nitrosonium ion, electrophilic aromatic substitution followed by oxidation reactions dominated over radical addition reactions for anisole. This ionic mechanism would predominate in urban atmospheric aerosols and nuclear fuel dissolutions. Irradiated neutral nitrate anisole solutions were dominated by mixed nitrosonium/nitronium ion electrophilic aromatic substitution reactions, but with lower product yields. Solutions such as these might be encountered in water treatment by e-beam irradiation. Irradiation of neutral nitrite anisole solutions resulted in a statistical substitution pattern for nitroanisole products, suggesting non-electrophilic free radical reactions involving the •NO2 radical. Although often proposed as an atmospheric nitrating agent, NO2 radical is unlikely to have an important effect in the acidic condensed phase in the presence of more reactive, competing species such as nitrous acid.

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