Product studies, kinetic isotope effect measurements, linear free energy relationships and calculations have been used to study the NO3-promoted nitration of toluene and phenol in presence of NO2. The competition between of a rate-determining hydrogen abstraction of NO3 to give the benzyl radical and HNO3 and of a rate-determining addition-elimination pathway has been evaluated. The preference for the nitration in ortho and para position of toluene and for the ortho position of phenol is suggested to derive from the concerted loss of nitric acid from an intermediate cyclohexadiene.A kinetic analysis suggests reasons for the dependence of the ratio ortho:para-nitration from the initial concentration of reactants
Product studies, kinetic isotope effect measurements, linear free energy relationships and calculations have been used to study the NO3-promoted nitration of toluene and phenol in presence of NO2. The competition between of a rate-determining hydrogen abstraction of NO3 to give the benzyl radical and HNO3 and of a rate-determining addition-elimination pathway has been evaluated. The preference for the nitration in ortho and para position of toluene and for the ortho position of phenol is suggested to derive from the concerted loss of nitric acid from an intermediate cyclohexadiene.A kinetic analysis suggests reasons for the dependence of the ratio ortho:para-nitration from the initial concentration of reactants
Bolzacchini, E., Bruschi, M., Galliani, G., Hjorth, J., Orlandi, M., Rindone, B. (2006). The regiochemistry of the NO3-promoted gas phase nitration of toluene and phenol with NO2. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 19(8-9), 570-578 [10.1002/poc.1060].
The regiochemistry of the NO3-promoted gas phase nitration of toluene and phenol with NO2
BOLZACCHINI, EZIO;BRUSCHI, MAURIZIO;ORLANDI, MARCO EMILIO;RINDONE, BRUNO
2006
Abstract
Product studies, kinetic isotope effect measurements, linear free energy relationships and calculations have been used to study the NO3-promoted nitration of toluene and phenol in presence of NO2. The competition between of a rate-determining hydrogen abstraction of NO3 to give the benzyl radical and HNO3 and of a rate-determining addition-elimination pathway has been evaluated. The preference for the nitration in ortho and para position of toluene and for the ortho position of phenol is suggested to derive from the concerted loss of nitric acid from an intermediate cyclohexadiene.A kinetic analysis suggests reasons for the dependence of the ratio ortho:para-nitration from the initial concentration of reactants
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
