Issue 4, 2011

Photochemical and photosensitised reactions involving 1-nitronaphthalene and nitrite in aqueous solution

Abstract

The excited triplet state of 1-nitronaphthalene, 1NN, (31NN) is able to oxidise nitrite to ˙NO2, with a second-order rate constant that varies from (3.56 ± 0.11) × 108 M−1 s−1 (μ ± σ) at pH 2.0 to (3.36 ± 0.28) × 109 M−1 s−1 at pH 6.5. The polychromatic quantum yield of ˙NO2 photogeneration by 1NN in neutral solution is Φ˙NO21NN ≥ (5.7 ± 1.5) × 107 × [NO2]/{(3.4 ± 0.3) × 109 × [NO2] + 6.0 × 105} in the wavelength interval of 300–440 nm. Irradiated 1NN is also able to produce ˙OH, with a polychromatic quantum yield Φ˙OH1NN = (3.42 ± 0.42) × 10−4. In the presence of 1NN and NO2/HNO2 under irradiation, excited 1NN (probably its triplet state) would react with ˙NO2 to yield two dinitronaphthalene isomers, 15DNN and 18DNN. The photonitration of 1NN is maximum around pH 3.5. At higher pH the formation rate of ˙NO2 by photolysis of NO2/HNO2 would be lower, because the photolysis of nitrite is less efficient than that of HNO2. At lower pH, the reaction between 31NN and ˙NO2 is probably replaced by other processes (involving e.g.31NN-H+) that do not yield the dinitronaphthalenes.

Graphical abstract: Photochemical and photosensitised reactions involving 1-nitronaphthalene and nitrite in aqueous solution

Supplementary files

Article information

Article type
Paper
Submitted
20 Oct 2010
Accepted
03 Jan 2011
First published
25 Jan 2011

Photochem. Photobiol. Sci., 2011,10, 601-609

Photochemical and photosensitised reactions involving 1-nitronaphthalene and nitrite in aqueous solution

P. Reddy Maddigapu, C. Minero, V. Maurino, D. Vione, M. Brigante, T. Charbouillot, M. Sarakha and G. Mailhot, Photochem. Photobiol. Sci., 2011, 10, 601 DOI: 10.1039/C0PP00311E

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