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

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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 300-44. 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.

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Authors and Affiliations

  1. Dipartimento di Chimica Analitica, Università di Torino, Via P. Giuria 5, 10125, Torino, Italy

    Pratap Reddy Maddigapu, Claudio Minero, Valter Maurino & Davide Vione

  2. Centro Interdipartimentale NatRisk, Università di Torino, Via Leonardo da Vinci 44, 10095, Grugliasco (TO), Italy

    Davide Vione

  3. Laboratoire de Photochimie Moléculaire et Macromoléculaire, Clermont Université, Université Blaise Pascal, BP 10448, F-63000, Clermont-Ferrand, France

    Marcello Brigante, Tiffany Charbouillot, Mohamed Sarakha & Gilles Mailhot

  4. CNRS, UMR 6505, Laboratoire de Photochimie Moléculaire et Macromol éculaire, F-63177, Aubière, France

    Marcello Brigante, Tiffany Charbouillot, Mohamed Sarakha & Gilles Mailhot

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  1. Pratap Reddy Maddigapu
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  2. Claudio Minero
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Correspondence to Davide Vione or Marcello Brigante.

Additional information

Electronic supplementary information (ESI) available: Effects of nitrite and pH on the decay of 31NN, pH trend of 1NN transformation rate, effects of 2-propanol and oxygen on the photonitration of 1NN.

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Maddigapu, P.R., Minero, C., Maurino, V. et al. Photochemical and photosensitised reactions involving 1-nitronaphthalene and nitrite in aqueous solution. Photochem Photobiol Sci 10, 601–609 (2011). https://doi.org/10.1039/c0pp00311e

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