Autoxidation of organic compounds in the atmosphere

Journal of Physical Chemistry Letters

Volumn 4, Issue 20, 2013, Pages 3513-3520

  Crounse, John D ^a   Nielsen, Lasse B ^c   Jørgensen, Solvejg ^c   Kjaergaard, Henrik G ^c   Wennberg, Paul O ^a,b  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b California Institute of Technology   (United States)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

aerosol aging; atmospheric oxidation; autoxidation; peroxy radicals

Indexed keywords

AB INITIO CALCULATIONS; AEROSOL AGING; ATMOSPHERIC AEROSOL PARTICLES; ATMOSPHERIC OXIDATION; AUTOXIDATION; INTRAMOLECULAR HYDROGEN; OXYGEN-CONTAINING FUNCTIONAL GROUPS; PEROXY RADICALS;

ABSTRACTING; ATMOSPHERIC AEROSOLS; FUNCTIONAL GROUPS; HYDROGEN;

OXIDATION;

EID: 84885988721     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz4019207     Document Type: Article

References (57)

1. Cox, R. A.; Cole, J. A. Chemical Aspects of the Autoignition of Hydrocarbon-Air Mixtures Combust. Flame 1985, 60, 109-123
2. Ingold, K. U. Inhibition of the Autoxidation of Organic Substances in the Liquid Phase Chem. Rev. 1961, 61, 563-589
3. Hathway, D. E.; Seakins, J. W. T. Autoxidation of Polyphenols. 3. Autoxidation in Neutral Aqueous Solution of Flavans Related to Catechin J Chem. Soc. 1957, 1562-1566
4. St Angelo, A. J. Lipid Oxidation in Foods Crit. Rev. Food Sci. 1996, 36, 175-224
5. Danilewicz, J. C. Mechanism of Autoxidation of Polyphenols and Participation of Sulfite in Wine: Key Role of Iron Am. J. Enol. Vitic. 2011, 62, 319-328
6. Bolland, J. L.; Koch, H. P. The Course of Autoxidation Reactions in Polyisoprenes and Allied Compounds. 9. The Primary Thermal Oxidation Product of Ethyl Linoleate J Chem. Soc. 1945, 445-447
7. Bolland, J. L. Kinetics of Olefin Oxidation Q. Rev. Chem. Soc. 1949, 3, 1-21
8. Porter, N. A. Mechanisms for the Autoxidation of Polyunsaturated Lipids Acc. Chem. Res. 1986, 19, 262-268
9. Ingold, K. U.; Bowry, V. W.; Stocker, R.; Walling, C. Autoxidation of Lipids and Antioxidation by α-Tocopherol and Ubiquinol in Homogeneous Solution and in Aqueous Dispersions of Lipids-Unrecognized Consequences of Lipid Particle-Size as Exemplified by Oxidation of Human Low-Density-Lipoprotein Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 45-49
10. Jimenez, J. L.; Canagaratna, M. R.; Donahue, N. M.; Prevot, A. S. H.; Zhang, Q.; Kroll, J. H.; DeCarlo, P. F.; Allan, J. D.; Coe, H.; Ng, N. L. Evolution of Organic Aerosols in the Atmosphere Science 2009, 326, 1525-1529
11. Zhang, Q.; Jimenez, J. L.; Canagaratna, M. R.; Allan, J. D.; Coe, H.; Ulbrich, I.; Alfarra, M. R.; Takami, A.; Middlebrook, A. M.; Sun, Y. L. Ubiquity and Dominance of Oxygenated Species in Organic Aerosols in Anthropogenically- Influenced Northern Hemisphere Midlatitudes Geophys. Res. Lett. 2007, 34, L13801
12. Murphy, D. M.; Cziczo, D. J.; Froyd, K. D.; Hudson, P. K.; Matthew, B. M.; Middlebrook, A. M.; Peltier, R. E.; Sullivan, A.; Thomson, D. S.; Weber, R. J. Single-Particle Mass Spectrometry of Tropospheric Aerosol Particles J. Geophys. Res.: Atmos. 2006, 111, D23S32
13. Donahue, N. M.; Robinson, A. L.; Stanier, C. O.; Pandis, S. N. Coupled Partitioning, Dilution, and Chemical Aging of Semivolatile Organics Environ. Sci. Technol. 2006, 40, 2635-2643
14. Kroll, J. H.; Seinfeld, J. H. Chemistry of Secondary Organic Aerosol: Formation and Evolution of Low-Volatility Organics in the Atmosphere Atmos. Environ. 2008, 42, 3593-3624
15. Lim, Y. B.; Tan, Y.; Perri, M. J.; Seitzinger, S. P.; Turpin, B. J. Aqueous Chemistry and Its Role in Secondary Organic Aerosol (SOA) Formation Atmos. Chem. Phys. 2010, 10, 10521-10539
16. George, I. J.; Chang, R. Y. W.; Danov, V.; Vlasenko, A.; Abbatt, J. P. D. Modification of Cloud Condensation Nucleus Activity of Organic Aerosols by Hydroxyl Radical Heterogeneous Oxidation Atmos. Environ. 2009, 43, 5038-5045
17. Chan, A. W. H.; Isaacman, G.; Wilson, K. R.; Worton, D. R.; Ruehl, C. R.; Nah, T.; Gentner, D. R.; Dallmann, T. R.; Kirchstetter, T. W.; Harley, R. A. Detailed Chemical Characterization of Unresolved Complex Mixtures in Atmospheric Organics: Insights into Emission Sources, Atmospheric Processing, and Secondary Organic Aerosol Formation J. Geophys. Res.: Atmos. 2013, 118, 6783-6796
18. O'Brien, R. E.; Laskin, A.; Laskin, J.; Liu, S.; Weber, R.; Russell, L. M.; Goldstein, A. H. Molecular Characterization of Organic Aerosol Using Nanospray Desorption/Electrospray Ionization Mass Spectrometry: Calnex 2010 Field Study Atmos. Environ. 2013, 68, 265-272
19. Ingold, K. U. Peroxy Radicals Acc. Chem. Res. 1969, 2, 1-9
20. 2: A Model for Radical-Initiated Oxidation of Organic Aerosols Phys. Chem. Chem. Phys. 2007, 9, 4803-4813
21. Rogge, W. F.; Hildemann, L. M.; Mazurek, M. A.; Cass, G. R.; Simonelt, B. R. T. Sources of Fine Organic Aerosol. 1. Charbroilers and Meat Cooking Operations Environ. Sci. Technol. 1991, 25, 1112-1125
22. Crounse, J. D.; Paulot, F.; Kjaergaard, H. G.; Wennberg, P. O. Peroxy Radical Isomerization in the Oxidation of Isoprene Phys. Chem. Chem. Phys. 2011, 13, 13607-13613
23. x Radical Regeneration in the Oxidation of Isoprene Phys. Chem. Chem. Phys. 2009, 11, 5935-5939
24. da Silva, G.; Graham, C.; Wang, Z.-F. Unimolecular β-Hydroxyperoxy Radical Decomposition with OH Recycling in the Photochemical Oxidation of Isoprene Environ. Sci. Technol. 2010, 44, 250-256
25. Atkinson, R.; Aschmann, S. M.; Carter, W. P. L.; Pitts, J. N. Rate Constants for the Gas-Phase Reaction of OH-Initiated Radicals with a Series of Ketones at 299 ± 2 K Int. J. Chem. Kinet. 1982, 14, 839-847
26. Wallington, T. J.; Kurylo, M. J. Flash-Photolysis Resonance Fluorescence Investigation of the Gas-Phase Reactions of OH-Initiated Radicals with a Series of Aliphatic-Ketones over the Temperature-Range 240-440 K J. Phys. Chem. 1987, 91, 5050-5054
27. Carter, W. P. L.; Atkinson, R. Alkyl Nitrate Formation from the Atmospheric Photooxidation of Alkanes-A Revised Estimation Method J. Atmos. Chem. 1989, 8, 165-173
28. Saunders, S. M.; Jenkin, M. E.; Derwent, R. G.; Pilling, M. J. Protocol for the Development of the Master Chemical Mechanism, MCM V3 (Part A): Tropospheric Degradation of Non-aromatic Volatile Organic Compounds Atmos. Chem. Phys. 2003, 3, 161-180
29. 2 J. Phys. Chem. A 2012, 116, 5756-5762
30. Vereecken, L.; Nguyen, T. L.; Hermans, I.; Peeters, J. Computational Study of the Stability of α-Hydroperoxyl-α-alkylperoxyl Substituted Alkyl Radicals Chem. Phys. Lett. 2004, 393, 432-436
31. Jorand, F.; Heiss, A.; Perrin, O.; Sahetchian, K.; Kerhoas, L.; Einhorn, J. Isomeric Hexyl-ketohydroperoxides Formed by Reactions of Hexoxy and Hexylperoxy Radicals in Oxygen Int. J. Chem. Kinet. 2003, 35, 354-366
32. Skold, M.; Borje, A.; Matura, M.; Karlberg, A. T. Studies on the Autoxidation and Sensitizing Capacity of the Fragrance Chemical Linalool, Identifying a Linalool Hydroperoxide Contact Dermatitis 2002, 46, 267-272
33. Christensson, J. B.; Forsstrom, P.; Wennberg, A.-M.; Karlberg, A.-T.; Matura, M. Air Oxidation Increases Skin Irritation from Fragrance Terpenes Contact Dermatitis 2009, 60, 32-40
34. Ehn, M.; Kleist, E.; Junninen, H.; Petaja, T.; Lonn, G.; Schobesberger, S.; Dal Maso, M.; Trimborn, A.; Kulmala, M.; Worsnop, D. R. Gas Phase Formation of Extremely Oxidized Pinene Reaction Products in Chamber and Ambient Air Atmos. Chem. Phys. 2012, 12, 5113-5127
35. Virtanen, A.; Joutsensaari, J.; Koop, T.; Kannosto, J.; Yli-Pirila, P.; Leskinen, J.; Makela, J. M.; Holopainen, J. K.; Poeschl, U.; Kulmala, M. An Amorphous Solid State of Biogenic Secondary Organic Aerosol Particles Nature 2010, 467, 824-827
36. Koop, T.; Bookhold, J.; Shiraiwa, M.; Poeschl, U. Glass Transition and Phase State of Organic Compounds: Dependency on Molecular Properties and Implications for Secondary Organic Aerosols in the Atmosphere Phys. Chem. Chem. Phys. 2011, 13, 19238-19255
37. Renbaum, L. H.; Smith, G. D. The Importance of Phase in the Radical-Initiated Oxidation of Model Organic Aerosols: Reactions of Solid and Liquid Brassidic Acid Particles Phys. Chem. Chem. Phys. 2009, 11, 2441-2451
38. Paulot, F.; Wunch, D.; Crounse, J. D.; Toon, G. C.; Millet, D. B.; DeCarlo, P. F.; Vigouroux, C.; Deutscher, N. M.; González Abad, G.; Notholt, J. Importance of Secondary Sources in the Atmospheric Budgets of Formic and Acetic Acids Atmos. Chem. Phys. 2011, 11, 1989-2013
39. Walser, M. L.; Park, J.; Gomez, A. L.; Russell, A. R.; Nizkorodov, S. A. Photochemical Aging of Secondary Organic Aerosol Particles Generated from the Oxidation of d-Limonene J. Phys. Chem. A 2007, 111, 1907-1913
40. Kang, E.; Root, M. J.; Toohey, D. W.; Brune, W. H. Introducing the Concept of Potential Aerosol Mass (PAM) Atmos. Chem. Phys. 2007, 7, 5727-5744
41. George, I. J.; Slowik, J.; Abbatt, J. P. D. Chemical Aging of Ambient Organic Aerosol from Heterogeneous Reaction with Hydroxyl Radicals Geophys. Res. Lett. 2008, 35, L13811
42. Kessler, S. H.; Nah, T.; Daumit, K. E.; Smith, J. D.; Leone, S. R.; Kolb, C. E.; Worsnop, D. R.; Wilson, K. R.; Kroll, J. H. OH-Initiated Heterogeneous Aging of Highly Oxidized Organic Aerosol J. Phys. Chem. A 2012, 116, 6358-6365
43. Crounse, J. D.; McKinney, K. A.; Kwan, A. J.; Wennberg, P. O. Measurement of Gas-Phase Hydroperoxides by Chemical Ionization Mass Spectrometry Anal. Chem. 2006, 78, 6726-6732
44. St Clair, J. M.; McCabe, D. C.; Crounse, J. D.; Steiner, U.; Wennberg, P. O. Chemical Ionization Tandem Mass Spectrometer for the In Situ Measurement of Methyl Hydrogen Peroxide Rev. Sci. Instrum. 2010, 81, 094102
45. Garden, A. L.; Paulot, F.; Crounse, J. D.; Maxwell-Cameron, I. J.; Wennberg, P. O.; Kjaergaard, H. G. Calculation of Conformationally Weighted Dipole Moments Useful in Ion-Molecule Collision Rate Estimates Chem. Phys. Lett. 2009, 474, 45-50
46. Kjaergaard, H. G.; Knap, H. C.; Ørnsø, K. B.; Jørgensen, S.; Crounse, J. D.; Paulot, F.; Wennberg, P. O. Atmospheric Fate of Methacrolein. 2. Formation of Lactone and Implications for Organic Aerosol Production J. Phys. Chem. A 2012, 116, 5763-5768
47. Gonzalez, C.; Schlegel, H. B. Reaction-Path Following in Mass-Weighted Internal Coordinates J. Phys. Chem. 1990, 94, 5523-5527
48. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A. Gaussian 09, revision A.1.; Gaussian Inc.: Wallingford, CT, 2009.
49. Adler, T. B.; Knizia, G.; Werner, H.-J. A Simple and Efficient CCSD(T)-F12 Approximation J. Chem. Phys. 2007, 127, 221106
50. Peterson, K. A.; Adler, T. B.; Werner, H.-J. Systematically Convergent Basis Sets for Explicitly Correlated Wavefunctions: The Atoms H, He, B-Ne, and Al-Ar J. Chem. Phys. 2008, 128, 084102
51. Lane, J. R.; Kjaergaard, H. G. Explicitly Correlated Intermolecular Distances and Interaction Energies of Hydrogen Bonded Complexes J. Chem. Phys. 2009, 131, 034307
52. Knizia, G.; Adler, T. B.; Werner, H.-J. Simplified CCSD(T)-F12 Methods: Theory and Benchmarks J. Chem. Phys. 2009, 130, 054104
53. Werner, H.-J.; Knowles, P. J.; Knizia, G.; Manby, F. R.; Schütz, M.; Celani, P.; Korona, T.; Lindh, R.; Mitrushenkov, A.; Rauhut, G.; MOLPRO, version 2010.1, A Package of Ab Initio Programs; 2010.
54. Henriksen, N. E.; Hansen, F. Y. Theories of Molecular Reaction Dynamics: The Microscopic Foundation of Chemical Kinetics; Oxford University Press: New York, 2008.
55. Eckart, C. The Penetration of a Potential Barrier by Electrons Phys. Rev. 1930, 35, 1303-1309
56. 2 Elimination of Alkenyl Peroxy Radicals J. Phys. Chem. A 2011, 115, 655-663
57. Zhang, F.; Dibble, T. S. Impact of Tunneling on Hydrogen-Migration of the n-Propylperoxy Radical Phys. Chem. Chem. Phys. 2011, 13, 17969-17977