The fast gas-phase reaction of NO3 radicals with phenol was found to yield 2-nitrophenol as the only relevant nitration product. The yield of this product was high and independent of the concentration of NO2 at the concentrations applied. In the presence of ozone, also significant amounts of 4-nitrophenol and p-benzoquinone were formed. The rate constant of the reaction between NO3 radicals and phenol was determined to be 5.8 x 10(-12) cm(3) molecule(-1) s(-1) The selective formation of 2-nitrophenol (2) is suggested to derive from either the concerted keto-enol tautomerism in the reaction of a phenoxy radical with NO2 or the concerted elimination of nitric acid from a cyclohexa-3,5-diene intermediate
Bolzacchini, E., Bruschi, M., Hjorth, J., Meinardi, S., Orlandi, M., Rindone, B., et al. (2001). Gas-phase reaction of phenol with NO3. ENVIRONMENTAL SCIENCE & TECHNOLOGY, 35(9), 1791-1797 [10.1021/es001290m].
Gas-phase reaction of phenol with NO3
BOLZACCHINI, EZIO;BRUSCHI, MAURIZIO;ORLANDI, MARCO EMILIO;RINDONE, BRUNO;
2001
Abstract
The fast gas-phase reaction of NO3 radicals with phenol was found to yield 2-nitrophenol as the only relevant nitration product. The yield of this product was high and independent of the concentration of NO2 at the concentrations applied. In the presence of ozone, also significant amounts of 4-nitrophenol and p-benzoquinone were formed. The rate constant of the reaction between NO3 radicals and phenol was determined to be 5.8 x 10(-12) cm(3) molecule(-1) s(-1) The selective formation of 2-nitrophenol (2) is suggested to derive from either the concerted keto-enol tautomerism in the reaction of a phenoxy radical with NO2 or the concerted elimination of nitric acid from a cyclohexa-3,5-diene intermediate
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