Anisole nitration during gamma-irradiation of aqueous nitrite and nitrate solutions: Free radical versus ionic mechanisms

Environmental Chemistry

Volumn 7, Issue 2, 2010, Pages 183-189

  Elias, Gracy ^a   Mincher, Bruce J ^a   Mezyk, Stephen P ^b   Cullen, Thomas D ^b   Martin, Leigh R ^a  

^a IDAHO NATIONAL LABORATORY   (United States)

^b CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

N centred radicals; nitronium ion; nitrosonium ion; radical chemistry

Indexed keywords

EID: 79251619980     PISSN: 14482517     EISSN: None     Source Type: Journal    
DOI: 10.1071/EN09109     Document Type: Article

References (44)

1. G. A. Olah, R. Malhotra, S. C. Narang, Nitration, Methods and Mechanisms 1989 (Wiley-VCH: New York). [see pp. 54, 11, 50, 129-134 and references therein]
2. D. Vione, V. Maurino, C. Minero, E. Pelizzetti, Nitration and photonitration of naphthalene in aqueous systems. Environ. Sci. Technol. 2005, 39, 1101. doi:10.1021/ES048855P
3. D. Vione, V. Maurino, C. Minero, E. Pelizzetti, New processes in the environmental chemistry of nitrite: nitration of phenol upon nitrite photoinduced oxidation. Environ. Sci. Technol. 2002, 36, 669. doi:10.1021/ES010101C
4. N. J. Bunce, L. Liu, J. Zhu, D. A. Lane, Reaction of naphthalene and its derivatives with hydroxyl radicals in the gas phase. Environ. Sci. Technol. 1997, 31, 2252. doi:10.1021/ES960813G
5. R. Atkinson, J. Arey, B. Zielinska, S. M. Aschmann, Kinetics and products of the gas-phase reactions of OH Radicals and N2O5 with naphthalene and biphenyl. Environ. Sci. Technol. 1987, 21, 1014. doi:10.1021/ES50001A017
6. P. Neta, R. E. Huie, Rate constants for reactions of NO3 radicals in aqueous solutions. J. Phys. Chem. 1986, 90, 4644. doi:10.1021/J100410A035
7. D. Vione, V. Maurino, C. Minero, E. Pelizzetti, Phenol photonitration upon UV irradiation of nitrite in aqueous solution I: Effects of oxygen and 2-propanol. Chemosphere 2001, 45, 893. doi:10.1016/S0045-6535(01)00035-2
8. H. Herrmann, Kinetics of aqueous phase reactions relevant for atmospheric chemistry. Chem. Rev. 2003, 103, 4691. doi:10.1021/CR020658Q
9. C. N. Kurucz, T. D. Waite, W. J. Cooper, The Miami Electron Beam Research Facility: a large scale wastewater treatment application. Radiat. Phys. Chem. 1995, 45, 299. doi:10.1016/0969-806X(94) 00075-1
10. J. Dzengel, J. Theurich, D. W. Bahnemann, Formation of nitroaromatic compounds in advanced oxidation processes: photoloysis versus photocatalysis. Environ. Sci. Technol. 1999, 33, 294. doi:10.1021/ES980358J
11. B. J. Mincher, S. P. Mezyk, W. F. Bauer, G. Elias, C. Riddle, D. R. Peterman, FPEX γ-radiolysis in the presence of nitric acid. Solv. Extr. Ion Exch. 2007, 25, 593. doi:10.1080/07366290701512477
12. V. Lamare, J. F. Dozol, F. Allain, H. Virelezier, C. Moulin, C. Jankowski, J. C. Tabet, Behavior of calix[4]arene crown 6 under irradiation, in ACS Symposium Series 757 (Eds G. J. Lumetta, A. S. Gopalan) 2005, Ch. 5 (American Chemical Society: Washington, DC).
13. C. Lamouroux, N. Aychet, A. Lelièvre, C. K. Jankowski, C. Moulin, High performance liquid chromatography with electrospray ionization mass spectroscopy and diode array detection in the identification and quantification of the degradation products of calix[4]arene crown 6 under radiolysis. Rapid Commun. Mass Spectrom. 2004, 18, 1493. doi:10.1002/RCM.1513
14. Z. Zhou, R. G. Parr, Activation hardness-new index for describing the orientation of electrophilic aromatic-substitution. J. Am. Chem. Soc. 1990, 112, 5720. doi:10.1021/JA00171A007
15. J. W. Barnett, R. B. Moodie, K. Schofield, J. B. Weston, R. G. Coombes, J. G. Golding, G. D. Tobin, Electrophilic aromatic substitution. Part 16. The nitration of anisole, o-methylanisole, and p-methylanisole in aqueous sulfuric acid. J. Chem. Soc., Perkin Trans. 1977, II, 248. doi:10.1039/P29770000248
16. G. A. Olah, N. A. Overchuk, Remarks on the nitronium salt nitration of toluene and benzene. Can. J. Chem. 1965, 43, 3279. doi:10.1139/V65-458
17. G. A. Olah, H. C. Lin, J. A. Olah, S. C. Narang, Electrophilic and free radical nitration of benzene and toluene with various nitrating agents. Proc. Natl. Acad. Sci. USA 1978, 75, 1045. doi:10.1073/PNAS.75.3.1045
18. T. A. Turney, G. A. Wright, Nitrous acid and nitrosation. Chem. Rev. 1959, 59, 497. doi:10.1021/CR50027A004
19. R. M. Schramm, F. H. Westheimer, The mechanism of the nitration of anisole. J. Am. Chem. Soc. 1948, 70, 1782. doi:10.1021/JA01185A036
20. E. Halfpenny, P. L. Robinson, The nitration and hydroxylation of aromatic compounds by pernitrous acid. J. Chem. Soc. 1952, 939. doi:10.1039/JR9520000939
21. A. I. Titov, The free radical mechanism of nitration. Tetrahedron 1963, 19, 557. doi:10.1016/S0040-4020(01)98544-8
22. L. V. Shastri, R. E. Huie, Rate constants for hydrogen abstraction reactions of NO3 in aqueous solution. Int. J. Chem. Kinet. 1990, 22, 505. doi:10.1002/KIN.550220507
23. Y. Katsumura, P. Y. Jiang, R. Nagaishi, T. Oishi, K. Ishigure, Pulse radiolysis study of aqueous nitric acid solutions. Formation, mechanism, yield and reactivity of NO3 radical. J. Phys. Chem. 1991, 95, 4435. doi:10.1021/J100164A050
24. 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.
25. S. P. Mezyk, D. M. Bartels, Temperature dependence of hydrogen atom reaction with nitrate and nitrite species in aqueous solution. J. Phys. Chem. A 1997, 101, 6233. doi:10.1021/JP970934I
26. J. A. LaVerne, S. M. Pimblott, Yields of hydroxyl radical and hydrated electron scavenging reactions in aqueous solutions of biological interest. Radiat. Res. 1993, 135, 16. doi:10.2307/3578391
27. G. L. Hug, Optical spectra of nonmetallic inorganic transient species in aqueous solution. NSRDS-NBS 69, 1981 (US National Bureau of Standards: Washington, DC).
28. O. Ito, S. Akiho, M. Iino, Kinetics for reactions of the nitrate radical (•NO3) with aldehydes in acetonitrile. J. Phys. Chem. 1989, 93, 4079. doi:10.1021/J100347A041
29. E. Baciocchi, T. Del Giacco, S. M. Murgia, G. V. Sebastiani, Rate and mechanism for the reaction of the nitrate radical with aromatic and alkylaromatic compounds in acetonitrile. J. Chem. Soc. Chem. Comm. 1987, 1246. doi:10.1039/C39870001246
30. M. Daniels, Radiation chemistry of the aqueous nitrate system. III. Pulse electron radiolysis of concentrated sodium nitrate solutions. J. Phys. Chem. 1969, 73, 3710. doi:10.1021/J100845A027
31. V. A. Benderskii, A. G. Krivenko, E. A. Ponomarev, N. V. Fridovich, Protonation rate constants of the NO2? 3 radical ion. Sov. Electrochem. 1987, 23, 1343.
32. Y. Katsumura, NO• 2 and NO• 3 radicals in radiolysis of nitric acid solutions, in N-centered radicals 1998, p. 397 (Wiley: New York).
33. P. Y. Jiang, R. Nagaishi, T. Yotsuyanagi, Y. Katsumura, I. Ishigure, Gamma;-radiolysis study of concentrated nitric acid solutions. J. Chem. Soc., Faraday Trans. 1994, 90, 93. doi:10.1039/FT9949000093
34. M. V. Vladimirova, I. A. Kulikov, I. Y. Savelév, Steady-state concentrations of nitrous acid in γ-irradiated nitric acid solutions. Khimiya Vysokikh Energii 1969, 3, 526.
35. L. R. Dix, R. B. Moodie, Nitrosation and nitrous acid-catalysed nitration of anisole and 2,6-dimethylanisole. J. Chem. Soc., Perkin Trans. 1986, II, 1097. doi:10.1039/P29860001097
36. J. H. Atherton, R. B. Moodie, D. R. Noble, B. O. Sullivan, Nitrosation of m-xylene, anisole, 4-nitrophenyl ether and toluene in trifluoroacetic acid or in acetic-sulfuric acid mixtures under nitric oxide. J. Chem. Soc., Perkin Trans. 1997, II, 663. doi:10.1039/A700935F
37. J. H. Ridd, Some unconventional pathways in aromatic nitration. Acta Chem. Scand. A 1998, 52, 11. doi:10.3891/ACTA.CHEM.SCAND. 52-0011
38. M. Lehnig, The mechanism of the nitration of donor-activated benzene with nitric and nitrous acid as studied by 15N CIDNP. Tetrahedron Lett. 1999, 40, 2299. doi:10.1016/S0040-4039(99)00277-4
39. E. Kozłowska-Milner, R. K. Broszkiewicz, Pulse radiolysis of HNO3 and HNO3 (aq). Radiat. Phys. Chem. 1978, 11, 253.
40. T. J. Sworski, R. W. Matthews, H. A. Mahlman, Radiation chemistry of concentrated NaNO3 solutions: dependence of G(HNO2) on NaNO3 concentration. Adv. Chem. Ser. 1968, 82, 164. doi:10.1021/BA-1968-0081.CH011
41. V. M. Grätzel, A. Henglein, J. Lilie, G. Beck, Pulsradiolysische Untersuchung einiger Elementarprozesse der oxydation und reduktion des Nitritions. Ber. Bunsenges. Phys. Chem. 1969, 73, 646.
42. K. Whitman, S. Lyons, R. Miller, D. Nett, P. Treas, A. Zante, R. W. Fessenden, M. D. Thomas, Y. Wang, Linear accelerator for radiation chemistry research at Notre Dame, in IEEE Proceedings of the 16th Conference on Particle Accelerators, Dallas, TX 1995, pp. 131-133 (Institute of Electrical and Electronics Engineers).
43. B. J. Mincher, S. P. Mezyk, L. R. Martin, A pulse radiolysis investigation of the reactions of tributyl phosphate with the radical products of aqueous nitric acid irradiation. J. Phys. Chem. A 2008, 112, 6275. doi:10.1021/JP802169V
44. G.V. Buxton, C. R. Stuart, Reevaluation of the thiocyanate dosimeter for pulse radiolysis. J. Chem. Soc., Faraday Trans. 1995, 91, 279. doi:10.1039/FT9959100279