title: Gas-phase reaction of phenol with NO3.
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) cm3 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.
authors.affiliation: Department of Environmental Sciences, University of Milano-Bicocca, Piazza della Scienza 1, I-20126 Milano, Italy.
authors.forename: E
authors.initials: E
authors.lastname: Bolzacchini
authors.forename: M
authors.initials: M
authors.lastname: Bruschi
authors.forename: J
authors.initials: J
authors.lastname: Hjorth
authors.forename: S
authors.initials: S
authors.lastname: Meinardi
authors.forename: M
authors.initials: M
authors.lastname: Orlandi
authors.forename: B
authors.initials: B
authors.lastname: Rindone
authors.forename: E
authors.initials: E
authors.lastname: Rosenbohm
mesh_terms: D000393:Air Pollutants / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D005740:Gases; D008956:Models, Chemical; D009589:Nitrogen Oxides / Q000737:chemistry*; D019800:Phenol / Q000737:chemistry*; D014874:Water Pollutants, Chemical / Q000032:analysis
chemical_list: D000393:Air Pollutants; D005609:Free Radicals; D005740:Gases; D009589:Nitrogen Oxides; D014874:Water Pollutants, Chemical; C031701:nitrogen trioxide; D019800:Phenol