The detailed modes of reaction of (RONO2)H+ (R = H, CH3 or C2H5) with benzene(C6X6, X = H, D) were determined by Fourier transform ion cyclotron resonance mass spectrometry. Irrespective of the structure and energy of the potentially nitrating (RONO2)H+ reactants, benzene nitration and oxidation are found to proceed by two-step mechanisms, involving a fast, preliminary electron and proton transfer between (RONO2)H+ and C6X6, followed by the rate-determining attack of the C6X6+ and C6X6H+ daughters on the nucleophilic centres of RONO2. These reaction pathways, predominant under isolated-pair conditions, are discussed and compared with classical acid-induced aromatic nitration patterns both in the gas phase at atmospheric pressure and in solution.

Ft-icr Studies of Gas-phase Ionic Nitration of Benzene - the Role of Electron-transfer and Proton-transfer Processes / M., Attina; Cacace, Fulvio; Speranza, Maurizio. - In: INTERNATIONAL JOURNAL OF MASS SPECTROMETRY AND ION PROCESSES. - ISSN 0168-1176. - STAMPA. - 117(1992), pp. 37-46.

Ft-icr Studies of Gas-phase Ionic Nitration of Benzene - the Role of Electron-transfer and Proton-transfer Processes

CACACE, Fulvio;SPERANZA, Maurizio
1992

Abstract

The detailed modes of reaction of (RONO2)H+ (R = H, CH3 or C2H5) with benzene(C6X6, X = H, D) were determined by Fourier transform ion cyclotron resonance mass spectrometry. Irrespective of the structure and energy of the potentially nitrating (RONO2)H+ reactants, benzene nitration and oxidation are found to proceed by two-step mechanisms, involving a fast, preliminary electron and proton transfer between (RONO2)H+ and C6X6, followed by the rate-determining attack of the C6X6+ and C6X6H+ daughters on the nucleophilic centres of RONO2. These reaction pathways, predominant under isolated-pair conditions, are discussed and compared with classical acid-induced aromatic nitration patterns both in the gas phase at atmospheric pressure and in solution.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11573/460810
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