Substrate and positional selectivity of the gas-phase nitration of substituted benzenes by protonated methyl nitrate. The first example of a well-behaved aromatic nitration by a gaseous cation

1986 ◽  
Vol 108 (2) ◽  
pp. 318-319 ◽  
Author(s):  
Marina. Attina ◽  
Fulvio. Cacace
Keyword(s):  
Gas Phase ◽  
Substituted Benzenes ◽  
Methyl Nitrate ◽  
Positional Selectivity ◽  
Aromatic Nitration

scholarly journals Is Aromatic Nitration Spin Density Driven?

Chemistry ◽  
2021 ◽  
Vol 3 (4) ◽  
pp. 1286-1301
Author(s):  
Amedeo Capobianco ◽  
Alessandro Landi ◽  
Andrea Peluso
Keyword(s):  
Electron Transfer ◽  
Gas Phase ◽  
Radical Pair ◽  
Theoretical Data ◽  
Point Of View ◽  
Positional Selectivity ◽  
Solvent Polarization ◽  
Quantum Chemical Computations ◽  
Aromatic Nitration

The mechanism of aromatic nitration is critically reviewed with particular emphasis on the paradox of the high positional selectivity of substitution in spite of low substrate selectivity. Early quantum chemical computations in the gas phase have suggested that the retention of positional selectivity at encounter-limited rates could be ascribed to the formation of a radical pair via an electron transfer step occurring before the formation of the Wheland intermediate, but calculations which account for the effects of solvent polarization and the presence of counterion do not support that point of view. Here we report a brief survey of the available experimental and theoretical data, adding a few more computations for better clarifying the role of electron transfer for regioselectivity.

Experimental Study on the Mechanism of Gas-Phase Aromatic Nitration by Protonated Methyl Nitrate

1994 ◽  
Vol 116 (21) ◽  
pp. 9535-9542 ◽  
Author(s):  
Massimiliano Aschi ◽  
Marina Attina ◽  
Fulvio Cacace ◽  
Andreina Ricci
Keyword(s):  
Experimental Study ◽  
Gas Phase ◽  
Methyl Nitrate ◽  
Aromatic Nitration

scholarly journals Observations of methyl nitrate in the lower stratosphere during STRAT: Implications for its gas phase production mechanisms

1998 ◽  
Vol 25 (11) ◽  
pp. 1891-1894 ◽  
Author(s):  
F. Flocke ◽  
E. Atlas ◽  
S. Madronich ◽  
S. M. Schauffler ◽  
K. Aikin ◽  
...  
Keyword(s):  
Gas Phase ◽  
Lower Stratosphere ◽  
Methyl Nitrate ◽  
Production Mechanisms ◽  
Phase Production

ChemInform Abstract: The Acidity of Chloro-Substituted Benzenes: A Comparison of Gas Phase, ab initio, and Kinetic Data.

ChemInform ◽  
2010 ◽  
Vol 33 (5) ◽  
pp. no-no
Author(s):  
Manfred Schlosser ◽  
Elena Marzi ◽  
Fabrice Cottet ◽  
Heinz H. Bueker ◽  
Nico M. M. Nibbering
Keyword(s):  
Ab Initio ◽  
Gas Phase ◽  
Kinetic Data ◽  
Substituted Benzenes

Aromatic Nitration at the Encounter Rate in the Gas Phase

1987 ◽  
Vol 26 (11) ◽  
pp. 1177-1178 ◽  
Author(s):  
Marina Attinà ◽  
Fulvio Cacace ◽  
Giulia de Petris
Keyword(s):  
Gas Phase ◽  
Encounter Rate ◽  
Aromatic Nitration
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