Synthesis and identification of dimethylnitronaphthalenes and ethylnitronaphthalenes to aid in their analysis in ambient air

Polycyclic Aromatic Compounds

Volumn 27, Issue 3, 2007, Pages 211-237

  Gallagher, Kathryn A ^a   Arey, Janet ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Ambient analyses; Dimethylnitronaphthalenes; Ethylnitronaphthalenes

Indexed keywords

MASS SPECTROMETRY;

AIR SAMPLES; AMBIENT AIR; AMBIENT ANALYZE; AMBIENTS; CAPILLARY COLUMNS; DIMETHYLNITRONAPHTHALENE; ELECTRON IMPACT MASS SPECTRA; ETHYLNITRONAPHTHALENE; RETENTION INDEX; SPECTRUM INDICES;

ISOMERS;

EID: 34250364323     PISSN: 10406638     EISSN: 15635333     Source Type: Journal    
DOI: 10.1080/10406630701386248     Document Type: Article

References (39)

1. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. 1984. Polynuclear Aromatic Compounds, Part 2, Carbon Blacks, Mineral Oils and Some Nitroarenes, Vol. 33, Lyon: World Health Organization, International Agency for Research on Cancer.
2. H. Tokiwa and Y. Ohnishi, Mutagenicity and Carcinogenicity of Nitroarenes and Their Sources in the Environment, CRC Critical Rev. Toxicol. 17 (1986):23-60.
3. P. Gupta, W. P. Harger, and J. Arey, The Contribution of Nitro- and Methylnitronaphthalenes to the Vapor-phase Mutagencity of Ambient Air Samples, Atmos. Environ. 30 (1996):3157-3166.
4. J. L. Durant, W. F. Busby, Jr., A. L. Lafleur, B. W. Penman, and C. L Crespi, Human Cell Mutagenicity of Oxygenated, Nitrated and Unsubstituted Polycyclic Aromatic Hydrocarbons Associated with Urban Aerosols, Mutat. Res. 371 (1996):123-157.
5. J. C. Sasaki, J. Arey, D. A. Eastmond, K. K. Parks, and A. J. Grosovsky, Genotoxicity Induced in Human Lymphoblasts by Atmospheric Reaction Products of Naphthalene and Phenanthrene, Mutat. Res. 393 (1997):23-35.
6. IPCS Environmental Health Criteria 229, Selected Nitro- and Nitro-oxy-polycyclic Aromatic Hydrocarbons, Geneva: World Health Organization, International Programme on Chemical Safety (2003).
7. x Episode in the Los Angeles Basin, Atmos. Environ. 21 (1987):1437-1444.
8. R. Atkinson, J. Arey, A. M. Winer, and B. Zielinska, A Survey of Ambient Concentrations of Selected Polycyclic Aromatic Hydrocarbons (PAH) at Various Locations in California. Contract No. A5-185-32. Final Report to California Air Resources Board, Sacramento (1988).
9. J. Arey, R. Atkinson, B. Zielinska, and P. A. McElroy, Diurnal Concentrations of Volatile Polycyclic Aromatic Hydrocarbons and Nitroarenes during a Photochemical Air Pollution Episode in Glendora, California, Environ. Sci. Technol. 23 (1989):321-327.
10. J. Arey, H. L. Bethel, F. Reisen, and W. H. Brune, Nitro-PAHs in Mexico City: Can Their Presence by Attributed to Hydroxyl Radical Reactions? Megacity Impacts on Air Quality, AGU Fall Meeting, San Francisco, CA, December 13-15, 2004.
11. F. Reisen and J. Arey, Atmospheric Reactions Influence Seasonal PAH and Nitro-PAH Concentrations in the Los Angeles Basin, Environ. Sci. Technol. 39 (2005): 64-73.
12. N. K. Wilson, T. R. McCurdy, and J. C. Chuang, Concentrations and Phase Distributions of Nitrated and Oxygenated Polycyclic Aromatic Hydrocarbons in Ambient Air, Atmos. Environ. 29 (1995):2575-2584.
13. A. Cecinato, Nitrated Polynuclear Aromatic Hydrocarbons in Ambient Air in Italy. A Brief Overview, J. Sep. Sci. 26 (2003):402-408.
14. J. Arey, Atmospheric Reactions of PAHs Including Formation of Nitroarenes, In PAHs and Related Compounds, A. H. Neilson, Ed. The Handbook of Environmental Chemistry, Volume 3, Part I, O. Hutzinger, Series Ed., (1998):347-385 (Berlin: Springer-Verlag).
15. J. Arey and R. Atkinson, Photochemical Reactions of PAHs in the Atmosphere: In PAHs an Ecotoxicological Perspective, P. E. T. Douben, Ed., (2003): 47-63 (West Sussex: John Wiley & Sons, Ltd.).
16. B. Zielinska and S. Samy, Analysis of Nitrated Polycyclic Aromatic Hydrocarbons, Anal. Bioanal. Chem. 386 (2006):883-890.
17. M. C. Papula-Peck, R. S. Marano, D. Schuetzle, T. L. Riley, C. V. Hampton, T. J. Prater, L. M. Skewes, T. E. Jensen, P. H. Ruehle, L. C. Bosch, and W. P. Duncan, Determination of Nitrated Polynuclear Aromatic Hydrocarbons in Particulate Extracts by Capillary Column Gas Chromatography with Nitrogen Selective Detection, Anal. Chem. 55 (1983): 1946-1954.
18. 5 and Their Occurrence in Ambient Air, Environ. Sci. Technol. 23 (1989):723-729.
19. F. Reisen, S. Wheeler, and J. Arey, Methyl and Dimethyl-/ethyl- nitronaphthalenes Measured in Ambient Air in Southern California, Atmos. Environ. 37 (2003):3653-3657.
20. 3 Radicals, Poly cyclic Aromatic Compounds, 27 (2007):15-40.
21. 3 Radical-initiated Reactions of Naphthalene, Environ. Sci. Technol. 31 (1997):3173-3179.
22. N. J. Bunce, L. Liu, J. Zhu, and D. A. Lane, Reaction of Naphthalene and Its Derivatives with Hydroxyl Radicals in the Gas Phase, Environ. Sci. Technol. 31 (1997):2252-2259.
23. P. Gupta, Master of Science Thesis in Environmental Toxicology, The Contribution of Methylnitronaplithalenes to the Vapor-Phase Mutagenicity Observed in Ambient Air Samples Collected at Redlands, California. University of California, Riverside (1995).
24. P. T. Phousongphouang and J. Arey, Rate Constants for the Gas-phase Reactions of a Series of Alkylnaphthalenes with the OH Radical, Envimn. Sci. Technol. 36 (2002): 1947-1952.
25. P. T. Phousongphouang and J. Arey, Rate Constants for the Gas-phase Reactions of a Series of Alkylnaphthalenes with the Nitrate Radical, Environ. Sci. Technol. 37 (2003):308-313.
26. J. Arey andB. Zielinska, High Resolution Gas Chromatography/Mass Spectrometry Analysis of the Environmental Pollutants Methylnitronaphthalenes, J. High Res. Chrom. 12 (1989):101-105.
27. H. A. Bamford, D. Z. Bezabeh, M. M. Schantz, S. A. Wise, and J. E. Baker, Determination and Comparison of Nitrated-polycyclic Aromatic Hydrocarbons Measured in Air and Diesel Particulate Reference Materials, Chemosphere. 50 (2003):575-587.
28. B. S. Crimmins and J. E. Baker, Improved GC/MS Methods for Measuring Hourly PAH and Nitro-PAH Concentrations in Urban Particulate Matter, Atmos. Environ. 40 (2006):6764-6779.
29. R. Atkinson, C. N. Plum, W. P. L. Carter, A. M. Winer, and J. N. Pitts, Jr., Rate Constants for the Gas-phase Reactions of Nitrate Radicals with a Series of Organics in Air at 298 ± 1 K, J. Phys. Chem. 88 (1984):1210-1215.
30. B. Zielinska, J. Arey, R. Atkinson, T. Ramdahl, A. M. Winer, and J. N. Pitts, Jr., Reaction of Dinitrogen Pentoxide with Fluoranthene, J. Am. Chem. Soc. 108 (1986):4126-4132.
31. K. A. Gallagher, Master of Science Thesis in Environmental Toxicology, The Synthesis of Dimethylnitronaphthalenes and Ethylnitronaphthalenes as an Aid to Their Identification in Ambient Air, University of California, Riverside (2006).
32. P. R. Wells and P. G. E. Alcorn, Proton Magnetic Resonance Spectra of Nitronaphthalenes in Dimethylacetamide Solution, Aust. J. Chem. 16 (1963): 1108-1118.
33. D. W. Miller, F. F. Evans, and P. P. Fu, Effect of a Nitro Group Geometry on the Proton NMR Chemical Shifts of Nitro Aromatics, Spectros. Int. J. 4 (1985):91-94.
34. D. Schuetzle and T. E. Jensen, Analysis of Nitrated Polycyclic Aromatic Hydrocarbons (Nitro-PAH) by Mass Spectrometry: In Nitrated Polycyclic Aromatic Hydrocarbons, C. M. White (Ed.) (1985):121-167, (Huethig, Heidelberg).
35. 6, Mutat. Res. 206 (1988):131-140.
36. L. Wang, Doctor of Philosophy Dissertation in Environmental Toxicology, Aspects of the Atmospheric Chemistry of Alkylnaplithalenes, Phenanthrene and their Atmospheric Reaction Products, University of California, Riverside (2006).
37. California Air Resources Board, data for Riverside-Rubidoux, www.arb.ca.gov.
38. D. L. Poster, L. C. Sander, and S. A. Wise, Chromatographic Methods of Analysis for the Determination of PAHs in Environmental Samples. In PAHs and Related Compounds, A. H. Neilson, Ed. The Handbook of Environmental Chemistry, Volume 3, Part I, O. Hutzinger, Series Ed., (1998): 77-135 (Berlin: Springer-Verlag).
39. O. Panic and T. Gorecki, Comprehensive Two-dimensional Gas Chromatography (GC × GC) in Environmental Analysis and Monitoring, Anal. Bioanal. Chem. 386 (2006):1013-1023.