Atmospheric Chemistry and Physics
www.atmos-chem-phys.net
1680-7316
1680-7324
10
3
2010
10.5194/acp-10-997-2010
http://www.atmos-chem-phys.net/10/997/2010/
http://www.atmos-chem-phys.net/10/997/2010/acp-10-997-2010.html
http://www.atmos-chem-phys.net/10/997/2010/acp-10-997-2010.pdf
997
1016
2010-02-01
Secondary organic material formed by methylglyoxal in aqueous aerosol mimics
N. Sareen
A. N. Schwier
E. L. Shapiro
D. Mitroo
V. F. McNeill
vfm2103@columbia.edu
Department of Chemical Engineering, Columbia University, New York, NY, USA
We show that methylglyoxal forms light-absorbing secondary organic material
in aqueous ammonium sulfate and ammonium nitrate solutions mimicking
tropospheric aerosol particles. The kinetics were characterized using UV-Vis
spectrophotometry. The results suggest that the bimolecular reaction of
methylglyoxal with an ammonium or hydronium ion is the rate-limiting step
for the formation of light-absorbing species, with <I>k</I><sub>NH4+</sub><sup>II</sup>=5×10<sup>−6</sup> M<sup>−1</sup> min<sup>−1</sup> and <I>k</I><sub>H3O+</sub><sup>II</sup>≤10<sup>−3</sup> M<sup>−1</sup> min<sup>−1</sup>. Evidence of aldol condensation products and
oligomeric species up to 759 amu was found using chemical ionization mass
spectrometry with a volatilization flow tube inlet (Aerosol-CIMS). Tentative
identifications of carbon-nitrogen species and a sulfur-containing compound
were also made using Aerosol-CIMS. Aqueous solutions of methylglyoxal, with
and without inorganic salts, exhibit significant surface tension depression.
These observations add to the growing body of evidence that dicarbonyl
compounds may form secondary organic material in the aerosol aqueous phase,
and that secondary organic aerosol formation via heterogeneous processes may
affect seed aerosol properties.
Adamson, A. W. and Gast, A. P.: Physical chemistry of surfaces, Wiley, New York, 1997.
Aiken, A. C., DeCarlo, P. F., Kroll, J. H., Worsnop, D. R., Huffman, J. A., Docherty, K. S., Ulbrich, I. M., Mohr, C., Kimmel, J. R., Sueper, D., Sun, Y., Zhang, Q., Trimborn, A., Northway, M., Ziemann, P. J., Canagaratna, M. R., Onasch, T. B., Alfarra, M. R., Prevot, A. S. H., Dommen, J., Duplissy, J., Metzger, A., Baltensperger, U., and Jimenez, J. L.: O/C and OM/OC ratios of primary, secondary, and ambient organic aerosols with high-resolution time-of-flight aerosol mass spectrometry, Environ. Sci. Technol., 42(12), 4478–4485, 2008.
Altieri, K. E., Seitzinger, S. P., Carlton, A. G., Turpin, B. J., Klein, G. C., and Marshall, A. G.: Oligomers formed through in-cloud methylglyoxal reactions: Chemical composition, properties, and mechanisms investigated by ultra-high resolution FT-ICR mass spectrometry, Atmos. Environ., 42(7), 1476–1490, 2008.
Anastasiadis, S. H., Chen, J. K., Koberstein, J. T., Siegel, A. F., Sohn, J. E., and Emerson, J. A.: The Determination of Interfacial-Tension by Video Image-Processing of Pendant Fluid Drops, J. Colloid Interface Sci., 119(1), 55–66, 1987.
Andreae, M. O. and Gelencsér, A.: Black carbon or brown carbon? The nature of light-absorbing carbonaceous aerosols, Atmos. Chem. Phys., 6, 3131–3148, 2006.
Anttila, T., Kiendler-Scharr, A., Tillman, R., and Mentel, T. F.: On the Reactive Uptake of Gaseous Compounds by Organic-Coated Aqueous Aerosols: Theoretical Analysis and Application to the Heterogeneous Hydrolysis of N2O5, J. Phys. Chem. A., 110(35), 10435–10443, 2006.
Archer, R. J. and La Mer, V. K.: The rate of evaporation of water through fatty acid monolayers, J. Phys. Chem., 59, 200–208, 1955.
Asa-Awuku, A., Sullivan, A. P., Hennigan, C. J., Weber, R. J., and Nenes, A.: Investigation of molar volume and surfactant characteristics of water-soluble organic compounds in biomass burning aerosol, Atmos. Chem. Phys., 8, 799–812, 2008.
Attygalle, A. B., Garcia-Rubio, S., Ta, J., and Meinwald, J.: Collisionally-induced dissociation mass spectra of organic sulfate anions, J. Chem. Soc.-Perkin Trans., 2(4), 498–506, 2001.
Barsanti, K. C. and Pankow, J. F.: Thermodynamics of the formation of atmospheric organic particulate matter by accretion reactions – 2. Dialdehydes, methylglyoxal, and diketones, Atmos. Environ., 39(35), 6597–6607, 2005.
Bayliss, N. S. and McRae, E. G.: Solvent Effects in the Spectra of Acetone, Crotonaldehyde, Nitromethane, and Nitrobenzene, J. Phys. Chem., 58, 1006–1011, 1954.
Betterton, E. A. and Hoffmann, M. R.: Henry Law Constants of Some Environmentally Important Aldehydes, Environ. Sci. Technol., 22(12), 1415–1418, 1988.
Blake, R. S., Monks, P. S., and Ellis, A. M.: Proton-Transfer Reaction Mass Spectrometry, Chem. Rev., 109(3), 861–896, 2009.
Bogan, M. J., Patton, E., Srivastava, A., Martin, S., Fergenson, D. P., Steele, P. T., Tobias, H. J., Gard, E. E., and Frank, M.: Online aerosol mass spectrometry of single micrometer-sized particles containing poly(ethylene glycol), Rapid Comm. Mass. Spec., 21, 1214–1220, 2007.
Canny, J.: A Computational Approach to Edge Detection, IEEE Trans. Patt. Anal. Mach. Intell., 8, 679–714, 1986.
Carlton, A. G., Turpin, B. J., Altieri, K. E., Seitzinger, S. P., Mathur, R., Roselle, S. J., and Weber, R. J.: CMAQ Model Performance Enhanced When In-Cloud Secondary Organic Aerosol is Included: Comparisons of Organic Carbon Predictions with Measurements, Environ. Sci. Technol., 42(23), 8798–8802, 2008.
Carlton, A. G., Turpin, B. J., Lim, H. J., Altieri, K. E., and Seitzinger, S.: Link between isoprene and secondary organic aerosol (SOA): Pyruvic acid oxidation yields low volatility organic acids in clouds, Geophys. Res. Lett., 33(6), L06822, doi:10.1029/2005GL025374, 2006.
Casale, M. T., Richman, A. R., Elrod, M. J., Garland, R. M., Beaver, M. R., and Tolbert, M. A.: Kinetics of acid-catalyzed aldol condensation reactions of aliphatic aldehydes, Atmos. Environ., 41(29), 6212–6224, 2007.
Chuang, P. Y., Charlson, R. J., and Seinfeld, J. H.: Kinetic limitations on droplet formation in clouds, Nature, 390(6660), 594–596, 1997.
Cruz, C. N. and Pandis, S. N.: A study of the ability of pure secondary organic aerosol to act as cloud condensation nuclei, Atmos. Environ., 31(15), 2205–2214, 1997.
De Haan, D. O., Corrigan, A. L., Smith, K. W., Stroik, D. R., Turley, J. J., Lee, F. E., Tolbert, M. A., Jimenez, J. L., Cordova, K. E., and Ferrell, G. R.: Secondary Organic Aerosol-Forming Reactions of Glyoxal with Amino Acids, Environ. Sci. Technol., 43(8), 2818–2824, 2009a.
De Haan, D. O., Tolbert, M. A., and Jimenez, J. L.: Atmospheric condensed-phase reactions of glyoxal with methylamine, Geophys. Res. Lett., 36, LL11819, doi:10.1029/2009GL037441, 2009b.
Denkenberger, K. A., Moffet, R. C., Holecek, J. C., Rebotier, T. P., and Prather, K. A.: Real-time, single-particle measurements of oligomers in aged ambient aerosol particles, Environ. Sci. Technol., 41(15), 5439–5446, 2007.
Duplissy, J., Gysel, M., Alfarra, M. R., Dommen, J., Metzger, A., Prevot, A. S. H., Weingartner, E., Laaksonen, A., Raatikainen, T., Good, N., Turner, S. F., McFiggans, G., and Baltensperger, U.: Cloud forming potential of secondary organic aerosol under near atmospheric conditions, Geophys.Res.Lett., 35, L03818, doi:10.1029/2007GL031075, 2008.
El Haddad, I., Yao Liu, Nieto-Gligorovski, L., Michaud, V., Temime-Roussel, B., Quivet, E., Marchand, N., Sellegri, K., and Monod, A.: In-cloud processes of methacrolein under simulated conditions – Part 2: Formation of secondary organic aerosol, Atmos. Chem. Phys., 9, 5107–5117, 2009.
Enders, C. and Sigurdsson, S.: The chemistry of humic acid formation under physiological conditions, V. Announcement: The introductory phase of the humic acid formation. A aldol condensation from methylglyoxal, Ber. Dtsch. Chem. Ges., 76, 562–565, 1943.
Engelhart, G. J., Asa-Awuku, A., Nenes, A., and Pandis, S. N.: CCN activity and droplet growth kinetics of fresh and aged monoterpene secondary organic aerosol, Atmos. Chem. Phys., 8, 3937–3949, 2008.
Feingold, G. and Chuang, P. Y.: Analysis of the influence of film-forming compounds on droplet growth: Implications for cloud microphysical processes and climate, J. Atmos. Sci., 59(12), 2006–2018, 2002.
Folkers, M., Mentel, T. F., and Wahner, A.: Influence of an organic coating on the reactivity of aqueous aerosols probed by the heterogeneous hydrolysis of N2O5, Geophys. Res. Lett., 30(12), 1644–1647, 2003.
Fu, T. M., Jacob, D. J., and Heald, C. L.: Aqueous-phase reactive uptake of dicarbonyls as a source of organic aerosol over eastern North America, Atmos. Environ., 43(10), 1814–1822, 2009.
Galloway, M. M., Chhabra, P. S., Chan, A. W. H., Surratt, J. D., Flagan, R. C., Seinfeld, J. H., and Keutsch, F. N.: Glyoxal uptake on ammonium sulphate seed aerosol: reaction products and reversibility of uptake under dark and irradiated conditions, Atmos. Chem. Phys., 9, 3331–3345, 2009.
Gao, S., Surratt, J. D., Knipping, E. M., Edgerton, E. S., Shahgholi, M., and Seinfeld, J. H.: Characterization of polar organic components in fine aerosols in the southeastern United States: Identity, origin, and evolution, J. Geophys. Res.-Atmos., 111(D14), D14314, doi:10.1029/2005JD006601, 2006.
Garland, R. M., Wise, M. E., Beaver, M. R., DeWitt, H. L., Aiken, A. C., Jimenez, J. L., and Tolbert, M. A.: Impact of palmitic acid coating on the water uptake and loss of ammonium sulfate particles, Atmos. Chem. Phys., 5, 1951–1961, 2005.
Gilardoni, S., Liu, S., Takahama, S., Russell, L. M., Allan, J. D., Steinbrecher, R., Jimenez, J. L., De Carlo, P. F., Dunlea, E. J., and Baumgardner, D.: Characterization of organic ambient aerosol during MIRAGE 2006 on three platforms, Atmos. Chem. Phys., 9, 5417–5432, 2009.
Gómez-González, Y., Surratt, J. D., Cuyckens, F., Szmigielski, R., Vermeylen, R., Jaoui, M., Lewandowski, M., Offenberg, J. H., Kleindienst, T. E., Edney, E. O., Blockhuys, F., Van Alsenoy, C., Maenhaut, W., and Claeys, M.: Characterization of organosulfates from the photooxidation of isoprene and unsaturated fatty acids in ambient aerosol using liquid chromatography/(-) electrospray ionization mass spectrometry, J. Mass Spec., 43(3), 371–382, 2008.
Grosjean, D., Williams, E. L., and Grosjean, E.: Atmospheric Chemistry of Isoprene and of its Carbonyl Products, Environ. Sci. Technol., 27(5), 830–840, 1993.
Hartz, K. E. H., Rosenorn, T., Ferchak, S. R., Raymond, T. M., Bilde, M., Donahue, N. M., and Pandis, S. N.: Cloud condensation nuclei activation of monoterpene and sesquiterpene secondary organic aerosol, J. Geophys. Res.-Atmos., 110(D14), D14208, doi:10.1029/2004JD005754, 2005.
Hearn, J. D., Lovett, A. J., and Smith, G. D.: Ozonolysis of oleic acid particles: evidence for a surface reaction and secondary reactions involving Criegee intermediates, Phys. Chem. Chem. Phys., 7(3), 501–511, 2005.
Hearn, J. D., Renbaum, L. H., Wang, X., and Smith, G. D.: Kinetics and Products from a reaction of Cl radicals with dioctyl sebacate (DOS) particles in O2: a model for radical-initiated oxidation of organic aerosols, Phys. Chem. Chem. Phys., 9, 1–11, 2007.
Hearn, J. D. and Smith, G. D.: A chemical ionization mass spectrometry method for the online analysis of organic aerosols, Anal. Chem., 76(10), 2820–2826, 2004a.
Hearn, J. D. and Smith, G. D.: Kinetics and product studies for ozonolysis reactions of organic particles using aerosol CIMS, J. Phys. Chem. A, 108(45), 10019–10029, 2004b.
Hearn, J. D. and Smith, G. D.: Measuring rates of reaction in supercooled organic particles with implications for atmospheric aerosol, Phys. Chem. Chem. Phys., 7(13), 2549–2551, 2005.
Hearn, J. D. and Smith, G. D.: A mixed-phase relative rates technique for measuring aerosol reaction kinetics, Geophys. Res. Lett., 33(17), L17805, doi:10.1029/2006GL026963, 2006a.
Hearn, J. D. and Smith, G. D.: Reactions and mass spectra of complex particles using Aerosol CIMS, Int. J. Mass Spec., 258(1–3), 95–103, 2006b.
Hearn, J. D. and Smith, G. D.: Ozonolysis of Mixed Oleic Acid/n-Docosane Particles: The Roles of Phase, Morphology, and Metastable States, J. Phys. Chem. A, 111(43), 11059–11065, 2007.
Ho, K. F., Cao, J. J., Lee, S. C., Kawamura, K., Zhang, R. J., Chow, J. C., and Watson, J. G.: Dicarboxylic acids, ketocarboxylic acids, and dicarbonyls in the urban atmosphere of China, J. Geophys. Res.-Atmos., 112(D22), D22S27, doi:10.1029/2006JD008011, 2007.
Iinuma, Y., Muller, C., Berndt, T., Boge, O., Claeys, M., and Herrmann, H.: Evidence for the existence of organosulfates from beta-pinene ozonolysis in ambient secondary organic aerosol, Environ. Sci. Technol., 41(19), 6678–6683, 2007.
International Critical Tables of Numerical Data, Physics, Chemistry, and Technology (1st Electronic Edition), edited by: Washburn, E. W., Knovel, Norwich, NY, 2003.
Jacobson, M. Z.: Isolating nitrated and aromatic aerosols and nitrated aromatic gases as sources of ultraviolet light absorption, J. Geophys. Res.-Atmos., 104(D3), 3527–3542, 1999.
Jacobson, M. Z.: Control of fossil-fuel particulate black carbon and organic matter, possibly the most effective method of slowing global warming, J. Geophys. Res.-Atmos., 107(D19), 4410, doi:10.1029/2001JD001376, 2002.
Jang, M. S., Czoschke, N. M., Lee, S., and Kamens, R. M.: Heterogeneous atmospheric aerosol production by acid-catalyzed particle-phase reactions, Science, 298(5594), 814–817, 2002.
Juza, J.: The pendant drop method of surface tension measurement: Equation interpolating the shape factor tables for several selected planes, Czech. J. Phys., 47(3), 351–357, 1997.
Kalberer, M., Paulsen, D., Sax, M., Steinbacher, M., Dommen, J., Prevot, A. S. H., Fisseha, R., Weingartner, E., Frankevich, V., Zenobi, R., and Baltensperger, U.: Identification of polymers as major components of atmospheric organic aerosols, Science, 303(5664), 1659–1662, 2004.
Kawamura, K., Kasukabe, H., and Barrie, L. A.: Source and reaction pathways of dicarboxylic acids, ketoacids and dicarbonyls in arctic aerosols: One year of observations, Atmos. Environ., 30(10–11), 1709–1722, 1996.
Kawamura, K. and Yasui, O.: Diurnal changes in the distribution of dicarboxylic acids, ketocarboxylic acids and dicarbonyls in the urban Tokyo atmosphere, Atmos. Environ., 39(10), 1945–1960, 2005.
Keene, W. C., Pszenny, A. A. P., Maben, J. R., Stevenson, E., and Wall, A.: Closure evaluation of size-resolved aerosol pH in the New England coastal atmosphere during summer, J. Geophys. Res.-Atmos., 109(D23), D23202, doi:10.1029/2004JD004801, 2004.
Kendall, R. A., Dunning, T. H., and Harrison, R. J.: Electron affinities of the first-row atoms revisited. Systematic basis sets and wave functions., J. Chem. Phys., 96(9), 6796–6806, 1992.
King, S. M., Rosenoern, T., Shilling, J. E., Chen, Q., and Martin, S. T.: Cloud condensation nucleus activity of secondary organic aerosol particles mixed with sulfate, Geophys. Res. Lett., 34(24), L24806, doi:10.2019/2007GL030390, 2007.
King, S. M., Rosenoern, T., Shilling, J. E., Chen, Q., and Martin, S. T.: Increased cloud activation potential of secondary organic aerosol for atmospheric mass loadings, Atmos. Chem. Phys., 9, 2959–2971, 2009.
Kiss, G., Tombacz, E., and Hansson, H. C.: Surface tension effects of humic-like substances in the aqueous extract of tropospheric fine aerosol, J. Atmos. Chem., 50(3), 279–294, 2005.
Kohler, H.: The nucleus in the growth of hygroscopic droplets, Trans. Faraday Soc., 32, 1152–1161, 1936.
Krizner, H. E., De Haan, D. O., and Kua, J.: Thermodynamics and Kinetics of Methylglyoxal Dimer Formation: A Computational Study, J. Phys. Chem. A, 113(25), 6994–7001, 2009.
Kroll, J. H., Ng, N. L., Murphy, S. M., Varutbangkul, V., Flagan, R. C., and Seinfeld, J. H.: Chamber studies of secondary organic aerosol growth by reactive uptake of simple carbonyl compounds, J. Geophys. Res.-Atmos., 110(D23), D23207, doi:10.1029/2005JD006004, 2005.
Kundu, S., Kawamura, K., Andreae, T. W., Hoffer, A., and Andreae, M. O.: Molecular distributions of dicarboxylic acids, ketocarboxylic acids and α-dicarbonyls in biomass burning aerosols: implications for photochemical production and degradation in smoke layers, Atmos. Chem. Phys. Discuss., 9, 19783–19815, 2009.
Lajohn, L. A., Christiansen, P. A., Ross, R. B., Atashroo, T., and Ermler, W. C.: Abinitio Relativistic Effective Potentials with Spin Orbit Operators .3. Rb Through Xe, J. Chem. Phys., 87(5), 2812–2824, 1987.
Li, Z. D., Williams, A. L., and Rood, M. J.: Influence of soluble surfactant properties on the activation of aerosol particles containing inorganic solute, J. Atmos. Sci., 55(10), 1859–1866, 1998.
Liggio, J., Li, S. M., and McLaren, R.: Reactive uptake of glyoxal by particulate matter, J. Geophys. Res.-Atmos., 110(D10), D10304, doi:10.1029/2004JD005113, 2005.
Lin, M., Walker, J., Geron, C., and Khlystov, A.: Organic nitrogen in PM$_2.5$ aerosol at a forest site in the Southeast US, Atmos. Chem. Phys. Discuss., 9, 17157–17181, 2009.
Loeffler, K. W., Koehler, C. A., Paul, N. M., and De Haan, D. O.: Oligomer formation in evaporating aqueous glyoxal and methyl glyoxal solutions, Environ. Sci. Technol., 40(20), 6318–6323, 2006.
Lund Myhre, C. E. and Nielsen, C. J.: Optical properties in the UV and visible spectral region of organic acids relevant to tropospheric aerosols, Atmos. Chem. Phys., 4, 1759–1769, 2004.
Lukács, H., Gelencsér, A., Hoffer, A., Kiss, G., Horváth, K., and Hartyáni, Z.: Quantitative assessment of organosulfates in size-segregated rural fine aerosol, Atmos. Chem. Phys., 9, 231–238, 2009.
Matijevic, E. and Pethica, B. A.: The properties of ionized monolayers, Part 1. Sodium dodecyl sulfate at the air/water interface, Trans. Faraday Soc., 54, 1383–1389, 1958.
McNeill, V. F., Wolfe, G. M., and Thornton, J. A.: The Oxidation of Oleate in Submicron Aqueous Salt Aerosols: Evidence of a Surface Process, J. Phys. Chem. A., 111, 1073–1083, 2007.
McNeill, V. F., Yatavelli, R. L. N., Thornton, J. A., Stipe, C. B., and Landgrebe, O.: Heterogeneous OH oxidation of palmitic acid in single component and internally mixed aerosol particles: vaporization and the role of particle phase, Atmos. Chem. Phys., 8, 5465–5476, 2008.
McNeill, V. F., Patterson, J., Wolfe, G. M., and Thornton, J. A.: The effect of varying levels of surfactant on the reactive uptake of N<sub>2</sub>O$_5$ to aqueous aerosol, Atmos. Chem. Phys., 6, 1635–1644, 2006.
Meller, R., Raber, W., Crowley, J. N., Jenkin, M. E., and Moortgat, G. K.: The Uv-Visible Absorption-Spectrum of Methylglyoxal, J. Photochem. Photobiol. A, 62(2), 163–171, 1991.
Michaud, V., El Haddad, I., Yao Liu, Sellegri, K., Laj, P., Villani, P., Picard, D., Marchand, N., and Monod, A.: In-cloud processes of methacrolein under simulated conditions – Part 3: Hygroscopic and volatility properties of the formed secondary organic aerosol, Atmos. Chem. Phys., 9, 5119–5130, 2009.
Muller, P.: Glossary of Terms Used in Physical Organic Chemistry (IUPAC Recommendations 1994), Pure Appl.Chem., 66(5), 1077–1184, 1994.
Nemet, I., Vikic-Topic, D., and Varga-Defterdarovic, L.: Spectroscopic studies of methylglyoxal in water and dimethylsulfoxide, Bioorg. Chem., 32(6), 560–570, 2004.
Nozière, B. and Cordova, A.: A novel catalyst for aldol condensation reaction, WO2009045156, 2007.
Nozière, B., Dziedzic, P., and Cordova, A.: Formation of secondary light-absorbing "fulvic-like" oligomers: A common process in aqueous and ionic atmospheric particles?, Geophys. Res. Lett., 34(21), L21812, doi:10.1029/2007GL031300, 2007.
Nozière, B., Dziedzic, P., and Córdova, A.: Common inorganic ions are efficient catalysts for organic reactions in atmospheric aerosols and other natural environments, Atmos. Chem. Phys. Discuss., 9, 1–21, 2009a.
Nozière, B., Dziedzic, P., and Cordova, A.: Products and Kinetics of the Liquid-Phase Reaction of Glyoxal Catalyzed by Ammonium Ions (NH4+), J. Phys. Chem. A, 113(1), 231–237, 2009b.
Nozière, B. and Esteve, W.: Light-absorbing aldol condensation products in acidic aerosols: Spectra, kinetics, and contribution to the absorption index, Atmos. Environ., 41(6), 1150–1163, 2007.
Paulsen, D., Dommen, J., Kalberer, M., Prevot, A. S. H., Richter, R., Sax, M., Steinbacher, M., Weingartner, E., and Baltensperger, U.: Secondary organic aerosol formation by irradiation of 1,3,5-trimethylbenzene-NOx-H2O in a new reaction chamber for atmospheric chemistry and physics, Environ. Sci. Technol., 39(8), 2668–2678, 2005.
Rosano, H. L. and La Mer, V. K.: The Rate of Evaporation of Water Through Monolayers of Esters, Acids, and Alcohols, J. Phys. Chem., 60, 348–353, 1956.
Ruehl, C. R., Chuang, P. Y., and Nenes, A.: Distinct CCN activation kinetics above the marine boundary layer along the California coast, Geophys. Res. Lett., 36, L15814, doi:10.1029/2009GL038839, 2009.
Russell, L. M., Takahama, S., Liu, S., Hawkins, L. N., Covert, D. S., Quinn, P. K., and Bates, T. S.: Oxygenated fraction and mass of organic aerosol from direct emission and atmospheric processing measured on the R/V Ronald Brown during TEXAQS/GoMACCS 2006, J. Geophys. Res.-Atmos., 114, D00F05, doi:10.1029/2008JD011275, 2009.
Saathoff, H., Naumann, K. H., Schnaiter, M., Schock, W., Mohler, O., Schurath, U., Weingartner, E., Gysel, M., and Baltensperger, U.: Coating of soot and (NH4)(2)SO4 particles by ozonolysis products of alpha-pinene, J. Aerosol Sci., 34(10), 1297–1321, 2003.
Salma, I., Ocskay, R., Varga, I., and Maenhaut, W.: Surface tension of atmospheric humic-like substances in connection with relaxation, dilution, and solution pH, J. Geophys. Res.-Atmos., 111(D23), D23205, doi:10.1029/2005JD007015, 2006.
Seinfeld, J. H. and Pandis, S. N.: Atmospheric Chemistry and Physics: from air pollution to climate change, Wiley, New York, 1998.
Sempere, R. and Kawamura, K.: Comparative Distributions of Dicarboxylic-Acids and Related Polar Compounds in Snow Rain and Aerosols from Urban Atmosphere, Atmos. Environ., 28(3), 449–459, 1994.
Setschenow, J. Z.: Uber Die Konstitution der Salzosungen auf Grund ihres Verhaltens zu Kohlensaure, Z. Physik. Chem., 4, 117–125, 1889.
Shapiro, E. L., Szprengiel, J., Sareen, N., Jen, C. N., Giordano, M. R., and McNeill, V. F.: Light-absorbing secondary organic material formed by glyoxal in aqueous aerosol mimics, Atmos. Chem. Phys., 9, 2289–2300, 2009.
Shulman, M. L., Jacobson, M. C., Carlson, R. J., Synovec, R. E., and Young, T. E.: Dissolution behavior and surface tension effects of organic compounds in nucleating cloud droplets, Geophys. Res. Lett., 23(3), 277–280, 1996.
Skoog, D. A., Holler, F. J., and Nieman, T. A.: Principles of Instrumental Analysis, Saunders College Publishing, New York, 1997.
Smith, D. F., Kleindienst, T. E., and Mciver, C. D.: Primary product distributions from the reaction of OH with m-, p-xylene, 1,2,4- and 1,3,5-trimethylbenzene, J. Atmos. Chem., 34(3), 339–364, 1999.
Sorjamaa, R., Svenningsson, B., Raatikainen, T., Henning, S., Bilde, M., and Laaksonen, A.: The role of surfactants in Köhler theory reconsidered, Atmos. Chem. Phys., 4, 2107–2117, 2004.
Stemmler, K., Vlasenko, A., Guimbaud, C., and Ammann, M.: The effect of fatty acid surfactants on the uptake of nitric acid to deliquesced NaCl aerosol, Atmos. Chem. Phys., 8, 5127–5141, 2008.
Surratt, J. D., Gómez-González, Y., Chan, A. W. H., Vermeylen, R., Shahgholi, M., Kleindienst, T. E., Edney, E. O., Offenberg, J. H., Lewandowski, M., Jaoui, M., Maenhaut, W., Claeys, M., Flagan, R. C., and Seinfeld, J. H.: Organosulfate formation in biogenic secondary organic aerosol, J. Phys. Chem. A, 112(36), 8345–8378, 2008.
Surratt, J. D., Kroll, J. H., Kleindienst, T. E., Edney, E. O., Claeys, M., Sorooshian, A., Ng, N. L., Offenberg, J. H., Lewandowski, M., Jaoui, M., Flagan, R. C., and Seinfeld, J. H.: Evidence for organosulfates in secondary organic aerosol, Environ. Sci. Technol., 41(2), 517–527, 2007.
Tang, I. N.: Thermodynamic and optical properties of mixed-salt aerosols of atmospheric importance, J. Geophys. Res.-Atmos., 102(D2), 1883–1893, 1997.
Tang, I. N. and Munkelwitz, H. R.: Water Activities, Densities, and Refractive-Indexes of Aqueous Sulfates and Sodium-Nitrate Droplets of Atmospheric Importance, J. Geophys. Res.-Atmos., 99(D9), 18801–18808, 1994.
Tang, I. N., Tridico, A. C., and Fung, K. H.: Thermodynamic and optical properties of sea salt aerosols, J. Geophys. Res.-Atmos., 102(D19), 23269–23275, 1997.
Taraniuk, I., Graber, E. R., Kostinski, A., and Rudich, Y.: Surfactant properties of atmospheric and model humic-like substances (HULIS), Geophys. Res. Lett., 34(16), L16807, doi:10.1029/2007GL029576, 2007.
Thornberry, T., Murphy, D. M., Thomson, D. S., de Gouw, J. A., Warneke, C., Bates, T. S., Quinn, P. K., and Coffman, D.: Measurement of Aerosol Organic Compounds Using a Novel Collection/Thermal-Desorption PTR-ITMS Instrument, Aerosol Sci. Technol., 43(5), 486–501, 2009.
Thornton, J. A. and Abbatt, J. P. D.: N2O5 Reaction on Sub-micron Sea Salt Aerosol: Effect of Surface Active Organics, J. Phys. Chem. A, 109(44), 10004–10012, 2005.
Tuazon, E. C., Macleod, H., Atkinson, R., and Carter, W. P. L.: Alpha-Dicarbonyl Yields from the Nox-Air Photooxidations of A Series of Aromatic-Hydrocarbons in Air, Environ. Sci. Technol., 20(4), 383–387, 1986.
Volkamer, R., Jimenez, J. L., San Martini, F., Dzepina, K., Zhang, Q., Salcedo, D., Molina, L. T., Worsnop, D. R., and Molina, M. J.: Secondary organic aerosol formation from anthropogenic air pollution: Rapid and higher than expected, Geophys. Res. Lett., 33(17), L17811, doi:10.1029/2006GL026899, 2006.
Volkamer, R., San Martini, F., Molina, L. T., Salcedo, D., Jimenez, J. L., and Molina, M. J.: A missing sink for gas-phase glyoxal in Mexico CIty: Formation of secondary organic aerosol, Geophys. Res. Lett., 34, L19807, doi:10.1029/2007GL030752, 2007.
Volkamer, R., Ziemann, P. J., and Molina, M. J.: Secondary Organic Aerosol Formation from Acetylene (C<sub>2</sub>H<sub>2</sub>): seed effect on SOA yields due to organic photochemistry in the aerosol aqueous phase, Atmos. Chem. Phys., 9, 1907–1928, 2009.
Zhang, Q., Jimenez, J. L., Worsnop, D. R., and Canagaratna, M.: A case study of urban particle acidity and its influence on secondary organic aerosol, Environ. Sci. Technol., 41(9), 3213–3219, 2007.
Zhao, J., Levitt, N. P., Zhang, R. Y., and Chen, J. M.: Heterogeneous reactions of methylglyoxal in acidic media: Implications for secondary organic aerosol formation, Environ. Sci. Technol., 40(24), 7682–7687, 2006.
Zhou, X. L. and Mopper, K.: Apparent Partition-Coefficients of 15 Carbonyl-Compounds Between Air and Seawater and Between Air and Fresh-Water – Implications for Air Sea Exchange, Environ. Sci. Technol., 24(12), 1864–1869, 1990.