Abstract
The phototransformation of 1-naphthol in aerated aqueous solution was investigated by means of product studies and laser flash photolysis. The quantum yield as measured at 313 nm was found to be equal to 3.2 × 10−2 in oxygen-saturated medium while being 10-fold lower in deoxygenated solution. The main photoproducts in aerated medium were 1,4-naphthoquinone, 2-hydroxy-1,4-naphthoquinone and 6-hydroxy-1,4-naphthoquinone. Traces of 1,2-naphthoquinone and 5-hydroxy-1,4-naphthoquinones were detected too. Solvated electrons were detected by laser flash photolysis. The quantum yield of monophotonic ionisation was found to be lower than that of 1-naphthol photolysis indicating that other reaction pathways took place. The mechanisms of naphthoquinones and hydroxynaphthoquinones formation are discussed.
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References
The Pesticide Manual, ed. C. D. S. Tomlin, British Crop Protection Council, Surrey, 12th edn., 2000.
N. E. Stewart, R. E. Millemann, W. P. Breese, Acute Toxicity of the insecticide sevin and its hydrolytic product 1-naphthol to some marine organisms, Trans. Am. Fish. Soc., 1967, 96, 25–30.
M. Lukeman, D. Veale, P. Wan, V. R. N. Munasinghe, J. E. T. Corrie, Photogeneration of 1,5-naphthoquinone methides via excited-state (formal) intramolecular proton transfer (ESIPT) and photodehydration of 1-naphthol derivatives in aqueous solution, Can. J. Chem., 2004, 82, 240–253.
S. P. Webb, L. A. Philips, S. W. Yeh, L. M. Tolbert, J. H. J. Clark, Picosecond kinetics of the excited-state, proton-transfer reaction of 1-naphthol in water, J. Phys. Chem., 1986, 90, 5154–5164.
J. F. Ireland, P. A. H. Wyatt, Acid–base properties of electronically excited states of organic molecules, Adv. Phys. Org. Chem., 1967, 12, 131–221.
H. Shizuka, H. Hagiwara, M. Fukushima, Laser flash photolysis study of the hydrogen atom transfer reaction from triplet 1-naphthol to ground benzophenone, J. Am. Chem. Soc., 1985, 107, 7816–7823.
R. A. Larson, S. A. Rounds, Photochemistry in aqueous surface layers: 1-naphthol, ACS Symp. Ser., 1987, 327, 206–214.
C. G. Hatchard, C. G. Packer, A new sensitive chemical actinometer. II. Potassium ferrioxalate as a standard chemical actinometer, Proc. R. Soc. London, Ser. A, 1956, A235, 518–536.
D. Vialaton, C. Richard, D. Baglio, A. B. Paya-Perez, Mechanism of the photochemical transformation of naphthalene in water, J. Photochem. Photobiol., A, 1999, 123, 15–19.
O Brahmia, Phototransformation en solution aqueuse du carbaryl, du 1-naphthol et de la 1,4-naphthoquinone. Etude de la dégradation du 1-naphthol en présence de substances humiques extraites de sols et de tourbières, PhD Thesis, Université Blaise Pascal, Clermont-Ferrand, France, 2004, Numéro d’ordre: 1496.
G. Grabner, personal communication.
E. J. Hart, J. W. Boag, Absorption spectrum of the hydrated electron in water and in aqueous solutions, J. Am. Chem. Soc., 1962, 84, 4090–4095.
G. V. Buxton, C. L. Greenstock, W. P. Helman, A. B. Ross, Critical Review of Rate Constants for Reactions of Hydrated Electrons, Hydrogen Atoms and Hydroxyl Radicals (OH/O-) in Aqueous Solution, J. Phys. Chem. Ref. Data, 1988, 17, 513–886.
C. Richard and G. Grabner, Mechanism of phototransformation of phenol and derivatives in aqueous solution, in Handbook of Environmental Chemistry, 1999, vol. 2, pt. L, pp. 217–240.
M. Ottolenghi, Electron ejection and fluorescence in aqueous ß-naphthol solutions, J. Am. Chem. Soc, 1963, 85, 3557–3562.
R. L. Groot, Triplet and radical formation as observed on flashing aromatic hydroxyl derivatives in liquid and solid solution, Mol. Photochem., 1971, 3, 1–22.
G. Porter, M. W. Windsor, The triplet state in fluid media, Proc. R. Soc. London, Ser. A, 1958, A 245, 238–258.
J. Audureau, C. Filiol, P Boule, J. Lemaire, Photolysis and photo-oxidation of phenol in aqueous solution, J. Chim. Phys., 1976, 73, 613–20.
The chemistry of the quinonoid compounds, ed. S. Patai, Wiley, Bristol, 1974.
O. Brahmia, C. Richard, Phototransformation of 1,4-naphthoquinone in aqueous solution, Photochem. Photobiol. Sci., 2003, 2, 1038–1043.
R. Zepp, Quantum yields for reaction of pollutants in dilute aqueous solution, Environ. Sci. Technol., 1978, 12, 327–329.
The phototransformation of chemicals in water: results of a ring test, European Centre for Ecotoxicology and Toxicology of Chemicals (ECETOC), Berlin, Technical report no. 12, 1984.
R. G. Zepp, D. M. Cline, Rates of direct photolysis in aquatic environment, Environ. Sci. Technol., 1977, 11, 359–366.
S. Canonica, M. Freiburghaus, Electron-Rich Phenols for Probing the Photochemical Reactivity of Freshwaters, Environ. Sci. Technol., 2001, 35, 690–695.
D. Vialaton, C. Richard, Phototransformation of aromatic pollutants in solar light: photolysis versus photosensitized reactions under natural water conditions, Aquat. Sci., 2002, 64, 207–215.
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Brahmia, O., Richard, C. Photochemical transformation of 1-naphthol in aerated aqueous solution. Photochem Photobiol Sci 4, 454–458 (2005). https://doi.org/10.1039/b504309c
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DOI: https://doi.org/10.1039/b504309c