Direct photolysis of carbonyl compounds dissolved in cloud and fog droplets

Atmospheric Chemistry and Physics

Volumn 13, Issue 18, 2013, Pages 9461-9477

  Epstein, S A ^a   Tapavicza, E ^a   Furche, F ^a   Nizkorodov, S A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL COMPOUND; CLOUD DROPLET; DISSOLUTION; FOG; OXIDATION; PHOTOLYSIS;

EID: 84884625076     PISSN: 16807316     EISSN: 16807324     Source Type: Journal    
DOI: 10.5194/acp-13-9461-2013     Document Type: Article

References (116)

1. Albaladejo, J., Ballesteros, B., Jimenez, E., Martin, P., and Martinez, E.: A PLP-LIF kinetic study of the atmospheric reactivity of a series of C4-C7 saturated and unsaturated aliphatic aldehydes with OH, Atmos. Environ., 36, 3231-3239, 2002. (Pubitemid 34742035)
2. Albinet, A., Minero, C., and Vione, D.: Photochemical generation of reactive species upon irradiation of rainwater: Negligible photoactivity of dissolved organic matter, Sci. Total Environ., 408, 3367-3373, doi:10.1016/j.scitotenv.2010.04.011, 2010a.
3. Albinet, A., Minero, C., and Vione, D.: Phototransformation processes of 2,4-dinitrophenol, relevant to atmospheric water droplets, Chemosphere, 80, 753-758, 2010b.
4. Amyes, T. L. and Richard, J. P.: Enzymatic catalysis of proton transfer at carbon: Activation of triosephosphate isomerase by phosphite dianion, Biochemistry, 46, 5841-5854, doi:10.1021/bi700409b, 2007. (Pubitemid 46764132)
5. Atkinson, R.: A structure-activity relationship for the estimation of rate constants for the gas-phase reactions of OH radicals with organic compounds, Int. J. Chem. Kinet., 19, 799-828, doi:10.1002/kin.550190903, 1987.
6. Atkinson, R., Tuazon, E. C., and Aschmann, S. M.: Atmospheric chemistry of 2-pentanone and 2-heptanone, Environ. Sci. Technol., 34, 623-631, doi:10.1021/es9909374, 2000. (Pubitemid 30106237)
7. Atkinson, R., Baulch, D. L., Cox, R. A., Crowley, J. N., Hampson, R. F., Hynes, R. G., Jenkin, M. E., Rossi, M. J., and Troe, J.: Evaluated kinetic and photochemical data for atmospheric chemistry: Volume II; gas phase reactions of organic species, Atmos. Chem. Phys., 6, 3625-4055, doi:10.5194/acp-6-3625-2006, 2006. (Pubitemid 44369557)
8. Bacher, C., Tyndall, G., and Orlando, J.: The atmospheric chemistry of glycolaldehyde, J. Atmos. Chem., 39, 171-189, doi:10.1023/a:1010689706869, 2001. (Pubitemid 32536955)
9. Bayliss, N. S. and McRae, E. G.: Solvent effects in the spectra of acetone, crotonaldehyde, nitromethane and nitrobenzene, J. Phys. Chem., 58, 1006-1011, doi:10.1021/j150521a018, 1954.
10. Bayrakçeken, F.: Sensitized phosphorescence studies of p-xylene + biacetyl system, an optical antenna, Spectrochim. Acta A, 66, 1267-1270, doi:10.1016/j.saa.2006.06.018, 2007. (Pubitemid 46330940)
11. Bell, R. P. and Gold, V.: The reversible hydration of carbonyl compounds, in: Adv. Phys. Org. Chem., Academic Press, 1-29, 1966.
12. Berger, R., Fischer, C., and Klessinger, M.: Calculation of the vibronic fine structure in electronic spectra at higher temperatures. 1. Benzene and pyrazine, J. Phys. Chem. A, 102, 7157-7167, doi:10.1021/jp981597w, 1998. (Pubitemid 128592801)
13. Betterton, E. A., and Hoffmann, M. R.: Henry's law constants of some environmentally important aldehydes, Environ. Sci. Technol., 22, 1415-1418, doi:10.1021/es00177a004, 1988. (Pubitemid 19002984)
14. Bowman, J. H., Barket, D. J., and Shepson, P. B.: Atmospheric chemistry of nonanal, Environ. Sci. Technol., 37, 2218-2225, 2003. (Pubitemid 36593045)
15. Brown, H. C., McDaniel, D. H., and Hafliger, O.: Determination of organic structures by physical methods, Dissociation Constants, edited by: Braude, E. A. and Nachod, F. C., v. 1, Academic Press, 1955.
16. Bunce, N. J., Lamarre, J., and Vaish, S. P.: Photorearrangement of azoxybenzene to 2-hydroxyazobenzene: A convenient chemical actinometer, Photochem. Photobiol., 39, 531-533, doi:10.1111/j.1751-1097.1984.tb03888.x, 1984.
17. Buschmann, H.-J., Füldner, H.-H., and Knoche, W.: The reversible hydration of carbonyl compounds in aqueous solution. Part i, the keto/gem-diol equilibrium, Berichte der Bunsengesellschaft für physikalische Chemie, 84, 41-44, doi:10.1002/bbpc.19800840109, 1980.
18. Buttery, R. G., Bomben, J. L., Guadagni, D. G., and Ling, L. C.: Volatilities of organic flavor compounds in foods, J. Agric. Food. Chem., 19, 1045-1048, doi:10.1021/jf60178a004, 1971.
19. Buxton, G. V., Greenstock, C. L., Helman, W. P., and Ross, A. B.: Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals in aqueous solution, J. Phys. Chem. Ref. Data, 17, 513-886, 1988.
20. Buxton, G. V., Malone, N. T., and Salmon, G. A.: Oxidation of glyoxal initiated by OH in oxygenated aqueous solution, J. Chem. Soc., Faraday Trans., 93, 2889-2891, 1997. (Pubitemid 127784926)
21. Calvert, J. G. and Pitts, J. N.: Photochemistry, Wiley, New York, NY, 625-626, 1966.
22. Cederstav, A. K. and Novak, B. M.: Investigations into the chemistry of thermodynamically unstable species. The direct polymerization of vinyl alcohol, the enolic tautomer of acetaldehyde, J. Am. Chem. Soc., 116, 4073-4074, doi:10.1021/ja00088a051, 1994. (Pubitemid 24980999)
23. Chen, J., Peijnenburg, W. J. G. M., Quan, X., and Yang, F.: Quantitative structure property relationships for direct photolysis quantum yields of selected polycyclic aromatic hydrocarbons, Sci. Total Environ., 246, 11-20, 2000. (Pubitemid 30038221)
24. Dagaut, P., Wallington, T. J., Liu, R., and Kurylo, M. J.: A kinetics investigation of the gas-phase reactions of OH radicals with cyclic ketones and diones: Mechanistic insights, J. Phys. Chem., 92, 4375-4377, 1988.
25. Dawson, R. M. C., Elliott, D. C., and Elliott, W. H.: Data for biochemical research, Oxford University Press on Demand, 1989.
26. Dearden, J. C. and Schüürmann, G.: Quantitative structureproperty relationships for predicting Henry's law constant from molecular structure, Environ. Toxicol. Chem., 22, 1755-1770, doi:10.1897/01-605, 2003. (Pubitemid 37337304)
27. Dierksen, M. and Grimme, S.: Density functional calculations of the vibronic structure of electronic absorption spectra, J. Chem. Phys., 120, 3544-3554, 2004.
28. Doussin, J. F. and Monod, A.: Structure-activity relationship for the estimation of OH-oxidation rate constants of carbonyl compounds in the aqueous phase, Atmos. Chem. Phys. Discuss., 13, 15949-15991, doi:10.5194/acpd-13-15949- 2013, 2013.
29. Encinas, M. V., Rufs, A. M., and Lissi, E. A.: Photochemistry of hydroxyalkanones in solution, J. Chem. Soc., Perkin Trans. 2, 457-460, 1985.
30. EPA HENRYWIN v3.20, US Environmental Protection Agency, 2011.
31. Epstein, S. A. and Nizkorodov, S. A.: A comparison of the chemical sinks of atmospheric organics in the gas and aqueous phase, Atmos. Chem. Phys., 12, 8205-8222, doi:10.5194/acp-12-8205- 2012, 2012.
32. Epstein, S. A., Shemesh, D., Tran, V. T., Nizkorodov, S. A., and Gerber, R. B.: Absorption spectra and photolysis of methyl peroxide in liquid and frozen water, J. Phys. Chem. A, 24, 6068-6077, 2012.
33. Ervens, B. and Volkamer, R.: Glyoxal processing by aerosol multiphase chemistry: Towards a kinetic modeling framework of secondary organic aerosol formation in aqueous particles, Atmos. Chem. Phys., 10, 8219-8244, doi:10.5194/acp-10-8219- 2010, 2010.
34. Ervens, B., George, C., Williams, J. E., Buxton, G. V., Salmon, G. A., Bydder, M., Wilkinson, F., Dentener, F., Mirabel, P., Wolke, R., and Herrmann, H.: Capram 2.4 (modac mechanism): An extended and condensed tropospheric aqueous phase mechanism and its application, J. Geophys. Res., 108, 4426, doi:10.1029/2002jd002202, 2003a.
35. Ervens, B., Gligorovski, S., and Herrmann, H.: Temperaturedependent rate constants for hydroxyl radical reactions with organic compounds in aqueous solutions, Phys. Chem. Chem. Phys., 5, 1811-1824, 2003b.
36. Ervens, B., Turpin, B. J., and Weber, R. J.: Secondary organic aerosol formation in cloud droplets and aqueous particles (aqSOA): A review of laboratory, field and model studies, Atmos. Chem. Phys., 11, 11069-11102, doi:10.5194/acp-11- 11069-2011, 2011.
37. Esposito, A., Lukas, A., Meany, J. E., and Pocker, Y.: The reversible enolization and hydration of pyruvate: Possible roles of keto, enol, and hydrated pyruvate in lactate dehydrogenase catalysis, Can. J. Chem., 77, 1108-1117, doi:10.1139/v99-071, 1999. (Pubitemid 129658856)
38. Facchini, M. C., Fuzzi, S., Zappoli, S., Andracchio, A., Gelencsér, A., Kiss, G., Krivácsy, Z., Mészáros, E., Hansson, H.-C., Alsberg, T., and Zebühr, Y.: Partitioning of the organic aerosol component between fog droplets and interstitial air, J. Geophys. Res., 104, 26821-26832, doi:10.1029/1999jd900349, 1999.
39. Fang, W., Gong, L., Zhang, Q., Cao, M., Li, Y., and Sheng, L.: Measurements of secondary organic aerosol formed from OHinitiated photo-oxidation of isoprene using online photoionization aerosol mass spectrometry, Environ. Sci. Tech., 46, 3898- 3904, doi:10.1021/es204669d, 2012.
40. Finlayson-Pitts, B. J. and Pitts, J. N.: Chemistry of the upper and lower atmosphere, Academic Press, San Diego, CA, USA, 93-128, 2000.
41. Fischer, M. and Warneck, P.: The dissociation constant of pyruvic acid: Determination by spectrophotometric measurements, Berichte der Bunsengesellschaft für physikalische Chemie, 95, 523-527, doi:10.1002/bbpc.19910950414, 1991.
42. Frelek, J., Kowalska, P., Masnyk, M., Kazimierski, A., Korda, A., Wóznica, M., Chmielewski, M., and Furche, F.: Circular dichroism and conformational dynamics of cephams and their carba and oxa analogues, Chem.-Eur. J., 13, 6732-6744, doi:10.1002/chem.200700127, 2007. (Pubitemid 47230987)
43. Frenkel, D. and Smit, B.: Understanding molecular simulation: From algorithms to applications, Elsevier Science, 153-158, 2001.
44. Furche, F. and Rappoport, D.: Computational photochemistry, Computational and theoretical chemistry, edited by: Olivucci, M., Elsevier, Amsterdam, 93-128, 2005.
45. Garcia-Jiminez, F., Zuniga, O. C., Garcia, Y. C., Cardenas, J., and Cuevas, G.: Experimental and theoretical study of the products from the spontaneous dimerization of dl- and d-glyceraldehyde, J. Brazil. Chem. Soc., 16, 467-476, 2005. (Pubitemid 41127821)
46. Gelencser, A. and Varga, Z.: Evaluation of the atmospheric significance of multiphase reactions in atmospheric secondary organic aerosol formation, Atmos. Chem. Phys., 5, 2823-2831, doi:10.5194/acp-5-2823-2005, 2005. (Pubitemid 41646220)
47. Glushonok, G. K., Petryaev, E. P., Turetskaya, E. A., and Shadyro, O. I.: Equilibrium between the molecular forms of glycolaldehyde and of DL-glyceraldehyde in aqueous solutions, Zh. Fiz. Khim., 60, 2960-2970, 1986.
48. Glushonok, G. K., Glushonok, T. G., Maslovskaya, L. A., and Shadyro, O. I.: A 1h and 13c nmr and uv study of the state of hydroxyacetone in aqueous solutions, Russ. J. Gen. Chem., 73, 1027-1031, doi:10.1023/b:rugc.0000007604. 91106.60, 2003. (Pubitemid 39011499)
49. Gubina, T. I., Pankratov, A. N., Labunskaya, V. I., and Rogacheva, S. M.: Self-oscillating reaction in the furan series, Chem. Heterocycl. Compd., 40, 1396-1401, doi:10.1007/s10593-005-0051-5, 2004. (Pubitemid 40394784)
50. Guthrie, J. P.: Hydration of thioesters. Evaluation of the freeenergy changes for the addition of water to some thioesters, rateequilibrium correlations over very wide ranges in equilibrium constants, and a new mechanistic criterion, J. Am. Chem. Soc., 100, 5892-5904, doi:10.1021/ ja00486a048, 1978.
51. Guzmán, M. I., Colussi, A. J., and Hoffmann, M. R.: Photoinduced oligomerization of aqueous pyruvic acid, J. Phys. Chem. A, 110, 3619-3626, doi:10.1021/jp056097z, 2006.
52. Guzmán, M. I., Hoffmann, M. R., and Colussi, A. J.: Photolysis of pyruvic acid in ice: Possible relevance to co and CO2 ice core record anomalies, J. Geophys. Res., 112, D10123, doi:10.1029/2006jd007886, 2007. (Pubitemid 47193625)
53. Hammond, G. S., Borduin, W. G., and Guter, G. A.: Chelates of beta-diketones. I. Enolization, ionization and spectra, J. Am. Chem. Soc., 81, 4682-4686, doi:10.1021/ja01526a058, 1959.
54. Haynes, W. M., CRC handbook of chemistry and physics, 93rd Edn., CRC Press, Boca Raton, FL, 6-1, 2012.
55. Hilal, S. H., Bornander, L. L., and Carreira, L. A.: Hydration equilibrium constants of aldehydes, ketones and quinazolines, QSAR Com. Sci., 24, 631-638, doi:10.1002/qsar.200430913, 2005. (Pubitemid 41074331)
56. Hine, J. and Mookerjee, P. K.: Structural effects on rates and equilibriums. Xix. Intrinsic hydrophilic character of organic compounds. Correlations in terms of structural contributions, J. Org. Chem., 40, 292-298, doi:10.1021/jo00891a006, 1975.
57. Hobbs, P. V.: Aerosol-cloud-climate interactions, Academic Press, San Diego, CA, 98-105, 1993.
58. Hoover, W. G.: Canonical dynamics: Equilibrium phase-space distributions, Phys. Rev. A: At. Mol. Opt. Phys., 31, 1695-1697, 1985.
59. Horowitz, A., Meller, R., and Moortgat, G. K.: The uv-vis absorption cross sections of the alpha-dicarbonyl compounds: Pyruvic acid, biacetyl and glyoxal, J. Photochem. Photobiol., A, 146, 19-27, doi:10.1016/S1010-6030(01) 00601-3, 2001. (Pubitemid 33618508)
60. Hummel, J. R. and Reck, R. A.: A global surface albedo model, J. Appl. Meteorol., 18, 239-253, 1979.
61. Ip, H. S. S., Huang, X. H. H., and Yu, J. Z.: Effective Henry's law constants of glyoxal, glyoxylic acid, and glycolic acid, Geophys. Res. Lett., 36, L01802, doi:10.1029/2008gl036212, 2009.
62. IUPAC, Data, C. O. E., Serjeant, E. P., and Dempsey, B.: Ionisation constants of organic acids in aqueous solution, Pergamon Press, 1979.
63. Jaoui, M., Corse, E., Kleindienst, T. E., Offenberg, J. H., Lewandowski, M., and Edney, E. O.: Analysis of secondary organic aerosol compounds from the photooxidation of d-limonene in the presence of NOx and their detection in ambient PM2.5, Environ. Sci. Tech., 40, 3819-3828, doi:10.1021/es052566z, 2006. (Pubitemid 43902380)
64. Jürgens, M., Jacob, F., Ekici, P., Friess, A., and Parlar, H.: Determination of direct photolysis rate constants and OH radical reactivity of representative odour compounds in brewery broth using a continuous flow-stirred photoreactor, Atmos. Environ., 41, 4571-4584, doi:10.1016/j.atmosenv.2007.03. 053, 2007. (Pubitemid 46824122)
65. Karickoff, S.W., Carreira, L. A., and Hilal, S. H.: SPARC performs automated reasoning in chemistry, v4.6, 2011.
66. Klamt, A. and Schurmann, G.: Cosmo: A new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient, J. Chem. Soc., Perkin Trans., 2, 799-805, 1993.
67. Kwok, E. S. C. and Atkinson, R.: Estimation of hydroxyl radical reaction rate constants for gas-phase organic compounds using a structure-reactivity relationship: An update, Atmos. Environ., 29, 1685-1695, 1995. (Pubitemid 26436793)
68. Larsen, M. C. and Vaida, V.: Near infrared photochemistry of pyruvic acid in aqueous solution, J. Phys. Chem. A, 116, 5840-5846, doi:10.1021/jp2087972, 2012.
69. Leermakers, P. A. and Vesley, G. F.: The photochemistry of alphaketo acids and alpha-keto esters. I. Photolysis of pyruvic acid and benzoylformic acid, J. Am. Chem. Soc., 85, 3776-3779, doi:10.1021/ja00906a013, 1963.
70. Li, S.-M., Macdonald, A. M., Leithead, A., Leaitch, W. R., Gong, W., Anlauf, K. G., Toom-Sauntry, D., Hayden, K., Bottenheim, J., and Wang, D.: Investigation of carbonyls in cloudwater during ICARTT, J. Geophys. Res.-Atmos., 113, D17206, doi:10.1029/2007JD009364, 2008.
71. Lim, Y. B., Tan, Y., Perri, M. J., Seitzinger, S. P., and Turpin, B. J.: Aqueous chemistry and its role in secondary organic aerosol (SOA) formation, Atmos. Chem. Phys., 10, 10521- 10539, doi:10.5194/acp-10-10521-2010, 2010.
72. Mackinney, G. and Temmer, O.: The deterioration of dried fruit. Iv. Spectrophotometric and polarographic studies, J. Am. Chem. Soc., 70, 3586-3590, doi:10.1021/ja01191a013, 1948.
73. Malik, M. and Joens, J. A.: Temperature dependent near-UV molar absorptivities of glyoxal and gluteraldehyde in aqueous solution, Spectrochim. Acta, Part A, 56, 2653-2658, 2000. (Pubitemid 32069783)
74. Martinez, A. M., Cushmac, G. E., and Rocek, J.: Chromic acid oxidation of cyclopropanols, J. Am. Chem. Soc., 97, 6502-6510, doi:10.1021/ja00855a036, 1975.
75. Mayer, B. and Madronich, S.: Actinic flux and photolysis in water droplets: Mie calculations and geometrical optics limit, Atmos. Chem. Phys., 4, 2241-2250, doi:10.5194/acp-4-2241-2004, 2004. (Pubitemid 40008493)
76. Meylan, W. M. and Howard, P. H.: Bond contribution method for estimating Henry's law constants, Environ. Toxicol. Chem., 10, 1283-1293, doi:10.1002/etc.5620101007, 1991.
77. Monod, A. and Doussin, J. F.: Structure-activity relationship for the estimation of OH-oxidation rate constants of aliphatic organic compounds in the aqueous phase: Alkanes, alcohols, organic acids and bases, Atmos. Environ., 42, 7611-7622, 2008.
78. Monod, A., Poulain, L., Grubert, S., Voisin, D., and Wortham, H.: Kinetics of OH-initiated oxidation of oxygenated organic compounds in the aqueous phase: New rate constants, structure activity relationships and atmospheric implications, Atmos. Environ., 39, 7667-7688, 2005.
79. Nissenson, P., Knox, C. J. H., Finlayson-Pitts, B. J., Phillips, L. F., and Dabdub, D.: Enhanced photolysis in aerosols: Evidence for important surface effects, Phys. Chem. Chem. Phys., 8, 4700-4710, doi:10.1039/B609219E, 2006.
80. Nissenson, P., Dabdub, D., Das, R., Maurino, V., Minero, C., and Vione, D.: Evidence of the water-cage effect on the photolysis of NO?3 and FeOH+2 . Implications of this effect and of H2O2 surface accumulation on photochemistry at the air-water interface of atmospheric droplets, Atmos. Environ., 44, 4859-4866, doi:10.1016/j.atmosenv.2010.08.035, 2010.
81. Nosé, S.: A molecular dynamics method for simulations in the canonical ensemble, Mol. Phys., 52, 255-268, doi:10.1080/00268978400101201, 1984.
82. Pavia, D. L.: Introduction to spectroscopy, Brooks/Cole, Belmont, CA, 390-411, 2009.
83. Perdew, J. P., Ernzerhof, M., and Burke, K.: Rationale for mixing exact exchange with density functional approximations, J. Chem. Phys., 105, 9982-9985, 1996a. (Pubitemid 126747886)
84. Perdew, J. P., Burke, K., and Ernzerhof, M.: Generalized gradient approximation made simple, Phys. Rev. Lett., 77, 3865-3868, 1996b. (Pubitemid 126631804)
85. Pocker, Y., Meany, J. E., Nist, B. J., and Zadorojny, C.: Reversible hydration of pyruvic acid. I. Equilibrium studies, J. Phys. Chem., 73, 2879-2882, doi:10.1021/j100843a015, 1969.
86. Raventos-Duran, T., Camredon, M., Valorso, R., Mouchel-Vallon, C., and Aumont, B.: Structure-activity relationships to estimate the effective Henry's law constants of organics of atmospheric interest, Atmos. Chem. Phys., 10, 7643-7654, doi:10.5194/acp- 10-7643-2010, 2010.
87. Renard, P., Siekmann, F., Gandolfo, A., Socorro, J., Salque, G., Ravier, S., Quivet, E., Clément, J.-L., Traikia, M., Delort, A.- M., Voisin, D., Vuitton, V., Thissen, R., and Monod, A.: Radical mechanisms of methyl vinyl ketone oligomerization through aqueous phase OH-oxidation: on the paradoxical role of dissolved molecular oxygen, Atmos. Chem. Phys., 13, 6473-6491, doi:10.5194/acp-13-6473-2013, 2013.
88. Renzetti, N. A. and Doyle, D. J.: The chemical nature of the particulate in irradiated automobile exhaust, J. Air Pollut. Control Assoc., 8, 293-296, 1959.
89. Rice, F. O.: The effect of solvent on the ultra violet absorption spectrum of a pure substance, J. Am. Chem. Soc., 42, 727-735, doi:10.1021/ja01449a009, 1920.
90. Rogers, J. D.: Rate constant measurements for the reaction of the hydroxyl radical with cyclohexene, cyclopentene, and glutaraldehyde, Environ. Sci. Technol., 23, 177-181, 1989. (Pubitemid 19045241)
91. Röhrig, U. F., Frank, I., Hutter, J., Laio, A., VandeVondele, J., and Rothlisberger, U.: QM/MM car-parrinello molecular dynamics study of the solvent effects on the ground state and on the first excited singlet state of acetone in water, Chem. Phys. Chem., 4, 1177-1182, doi:10.1002/cphc.200300650, 2003.
92. Sander, R.: Compilation of Henry's law constants for inorganic and organic species of potential importance in environmental chemistry (version 3), http://www.henrys-law.org, (last access: 1 June 2013), 1999.
93. Sander, S. P., Abbatt, J., Barker, J. R., Burkholder, J. B., Friedl, R. R., Golden, D. M., Huie, R. E., Kolb, C. E., Kurylo, M. J., Moortgat, G. K., Orkin, V. L., andWine, P. H.: Chemical kinetics and photochemical data for use in atmospheric studies: Evaluation number 17. JPL Publication 10-6, Jet Propulsion Laboratory, Pasadena, http://jpldataeval.jpl.nasa.gov 5 June 2013, 2011.
94. Saxena, P. and Hildemann, L. M.: Water-soluble organics in atmospheric particles: A critical review of the literature and application of thermodynamics to identify candidate compounds, J. Atmos. Chem., 24, 57-109, 1996.
95. Schaefer, T., Schindelka, J., Hoffmann, D., and Herrmann, H.: Laboratory kinetic and mechanistic studies on the OH-initiated ox-idation of acetone in aqueous solution, J. Phys. Chem. A, 116, 6317-6326, doi:10.1021/jp2120753, 2012.
96. Schafer, A., Horn, H., and Ahlrichs, R.: Fully optimized contracted gaussian basis sets for atoms Li to Kr, J. Chem. Phys., 97, 2571-2577, 1992.
97. Schutze,M. and Herrmann, H.: Uptake of acetone, 2-butanone, 2,3- butanedione and 2-oxopropanal on a water surface, Phys. Chem. Chem. Phys., 6, 965-971, 2004.
98. Seinfeld, J. and Pandis, S.: Atmospheric chemistry and physics, John Wiley and Sons, Inc., New York, 1998.
99. Sham, Y. Y. and Joens, J. A.: Temperature dependent near uv molar absorptivities of several small aldehydes in aqueous solution, Spectrochim. Acta A, 51, 247-251, 1995.
100. Staffelbach, T. A., Orlando, J. J., Tyndall, G. S., and Calvert, J. G.: The uv-visible absorption spectrum and photolysis quantum yields of methylglyoxal, J. Geophys. Res. Atmos., 100, 14189-14198, doi:10.1029/95JD00541, 1995.
101. Staudinger, J. and Roberts, P. V.: A critical review of Henry's law constants for environmental applications, Crit. Rev. Environ. Sci. Technol., 26, 205-297, doi:10.1080/10643389609388492, 1996. (Pubitemid 26307214)
102. Steenken, S., Jaenicke-Zauner, W., and Schulte-Frohlinde, D.: Photofragmentation of hydroxyacetone, 1.3-dihydroxyacetone, and 1.3-dicarboxyacetone in aqueous solution. An EPR study, Photochem. Photobiol., 21, 21-26, doi:10.1111/j.1751- 1097.1975.tb06624.x, 1975.
103. Sulpizi, M., Carloni, P., Hutter, J., and Rothlisberger, U.: A hybrid TDDFT/MM investigation of the optical properties of aminocoumarins in water and acetonitrile solution, Phys. Chem. Chem. Phys., 5, 4798-4805, doi:10.1039/B305846H, 2003.
104. Tan, Y., Lim, Y. B., Altieri, K. E., Seitzinger, S. P., and Turpin, B. J.: Mechanisms leading to oligomers and SOA through aqueous photooxidation: Insights from OH radical oxidation of acetic acid and methylglyoxal, Atmos. Chem. Phys., 12, 801-813, doi:10.5194/acp-12-801-2012, 2012.
105. Tapavicza, E., Meyer, A. M., and Furche, F.: Unravelling the details of vitamin d photosynthesis by non-adiabatic molecular dynamics simulations, Phys. Chem. Chem. Phys., 13, 20986-20998, doi:10.1039/C1CP21292C, 2011.
106. Tapavicza, E., Vincent, J. C., Bellchambers, G. D., and Furche, F.: Ab initio non-adiabatic molecular dynamics Phys. Chem. Chem. Phys., doi:10.1039/C3CP51514A, 2013.
107. Treutler, O. and Ahlrichs, R.: Efficient molecular numerical integration schemes, J. Chem. Phys., 102, 346-354, 1995.
108. Turýan, Y. I.: Kinetics and equilibrium of the dehydration-hydration and recombination dissociation reactions of glyoxylic acid investigated by electrochemical methods, Croat. Chem. Acta, 71, 727-743, 1998.
109. van Pinxteren, D., Plewka, A., Hofmann, D., Müller, K., Kramberger, H., Svrcina, B., Bächmann, K., Jaeschke, W., Mertes, S., Collett Jr, J. L., and Herrmann, H.: Schmücke hill cap cloud and valley stations aerosol characterisation during FEBUKO (ii): Organic compounds, Atmos. Environ., 39, 4305-4320, doi:10.1016/j.atmosenv.2005.02.014, 2005.
110. Vione, D., Maurino, V., Minero, C., Pelizzetti, E., Harrison, M. A. J., Olariu, R.-I., and Arsene, C.: Photochemical reactions in the tropospheric aqueous phase and on particulate matter, Chem. Soc. Rev., 35, 441-453, doi:10.1039/b510796m, 2006. (Pubitemid 44004948)
111. Wallington, T. J., and Kurylo, M. J.: Flash photolysis resonance fluorescence investigation of the gas-phase reactions of OH radicals with a series of aliphatic ketones over the temperature range 240-440 k, J. Phys. Chem., 91, 1987.
112. Weigend, F. and Häser, M.: RI-MP2: First derivatives and global consistency, Theor. Chem. Acc., 97, 331-340, doi:10.1007/s002140050269, 1997. (Pubitemid 127136416)
113. Winkelman, J. G. M., Voorwinde, O. K., Ottens, M., Beenackers, A. A. C. M., and Janssen, L. P. B. M.: Kinetics and chemical equilibrium of the hydration of formaldehyde, Chem. Eng. Sci., 57, 4067-4076, 2002. (Pubitemid 35353050)
114. Xu, H., Wentworth, P. J., Howell, N. W., and Joens, J. A.: Temperature dependent near-uv molar absorptivities of aliphatic aldehydes and ketones in aqueous solution, Spectrochim. Acta A, 49, 1171-1178, 1993.
115. Zhou, S. M., Barnes, I., Zhu, T., Bejan, I., Albu, M., and Benter, T.: Atmospheric chemistry of acetylacetone, Environ. Sci. Technol., 42, 7905-7910, 2008.
116. Zhou, X. and Mopper, K.: Apparent partition coefficients of 15 carbonyl compounds between air and seawater and between air and freshwater; implications for air-sea exchange, Environ. Sci. Tech., 24, 1864-1869, doi:10.1021/ es00082a013, 1990.