The mechanisms for OH-initiated acenaphthylene degradation reactions are investigated theoretically by using the density function theory method at M06-2X/aug-cc-pVTZ level in the present paper. There are two possible reaction pathways for the degradation processes have been predicted: the hydrogen abstraction pathway and the hydroxyl addition elimination pathway. Additionally, the formation mechanism for a series of the products such as epoxide, naphthalene-1,8-dicarbaldehyde, dialdehydes, 1-acenaphthenone and nitroacenaphthylene are discussed in detail as well. From the analyses of the decomposition of OH-acenaphthylene adducts, it is found that the favorable reaction with O2/NO is to form the acenaphthenone rather than epoxide, and the most stable isomer is acenaphthenone react from the C1-site reaction. The advantage reaction pathway with NO2 is to form nitroacenaphthylene and nitroacenaphthylenol from C1-site, too.
References
[1]
Atkinson, R. (1990) Gas-Phase Tropospheric Chemistry of Organic Compounds: A Review. Atmospheric Environment. Part A. General Topics, 24, 1-41.
https://doi.org/10.1016/0960-1686(90)90438-S
[2]
Motorykin, O., Matzke, M.M., Waters, K.M. and Massey Simonich, S.L. (2013) Association of Carcinogenic Polycyclic Aromatic Hydrocarbon Emissions and Smoking with Lung Cancer Mortality Rates on a Global Scale. Environmental Science & Technology, 47, 3410-3416.
[3]
Dang, J., Shi, X.L., Hu, J.T., Chen, J.M., Zhang, Q.Z. and Wang, W.X. (2015) Mechanistic and Kinetic Studies on OH-Initiated Atmospheric Oxidation Degradation of Benzo[α]pyrene in the Presence of O2 and NOx. Chemosphere, 119, 387-393.
https://doi.org/10.1016/j.chemosphere.2014.07.001
[4]
Arey, J., Zielinska, B., Atkinson, R. and Aschmann, S.M. (1989) Nitroarene Products from the Gas-Phase Reactions of Volatile Polycyclic Aromatic Hydrocarbons with the OH Radical and N2O5. International Journal of Chemical Kinetics, 21, 775-799.
https://doi.org/10.1002/kin.550210906
[5]
Nishioka, M.G., Howard, C.C., Contos, D.A., Ball, L.M. and Lewtas, J. (1988) Detection of Hydroxylated Nitro Aromatic and Hydroxylated Nitro Polycyclic Aromatic Compounds in an Ambient Air Particulate Extract Using Bioassay-Directed Fractionation. Environmental Science & Technology, 22, 908-915. https://doi.org/10.1021/es00173a007
[6]
Yamasaki, H., Kuwata, K. and Miyamoto, H. (1982) Effects of Ambient Temperature on Aspects of Airborne Polycyclic Aromatic Hydrocarbons. Environmental Science & Technology, 16, 189-194. https://doi.org/10.1021/es00098a003
[7]
Atkinson, R. and Arey, J. (1994) Atmospheric Chemistry of Gas-Phase Polycyclic Aromatic Hydrocarbons: Formation of Atmospheric Mutagens. Environmental Health Perspectives, 102, 117-126. https://doi.org/10.1289/ehp.94102s4117
[8]
Atkinson, R., Aschmann, S.M., Arey, J., Barbara, Z. and Schuetzle, D. (1989) Gas-Phase Atmospheric Chemistry of 1- and 2-Nitronaphthalene and 1,4-Naphthoquinone. Atmospheric Environment, 23, 2679-2690. https://doi.org/10.1016/0004-6981(89)90548-9
[9]
Qu, X.H., Zhang, Q.Z. and Wang, W.X. (2006) Mechanism for OH-Initiated Photooxidation of Naphthalene in the Presence of O2 and NOx: A DFT Study. Chemical Physics Letters, 429, 77-85. https://doi.org/10.1016/j.cplett.2006.08.036
[10]
Shiroudi, A. and Deleuze, M.S. (2014) Theoretical Study of the Oxidation Mechanisms of Naphthalene Initiated by Hydroxyl Radicals: The H Abstraction Pathway. The Journal of Physical Chemistry A, 118, 3625-3636. https://doi.org/10.1021/jp500124m
[11]
Shiroudi, A., Deleuze, M.S. and Canneaux, S. (2014) Theoretical Study of the Oxidation Mechanisms of Naphthalene Initiated by Hydroxyl Radicals: The OH-Addition Pathway. The Journal of Physical Chemistry A, 118, 4593-4610. https://doi.org/10.1021/jp411327e
[12]
Zhang, Q.Z., Gao, R., Xu, F., Zhou, Q., Jiang, G.B., Wang, T., Chen, J.M., Hu, J.T., Jiang, W. and Wang, W.X. (2014) Role of Water Molecule in the Gas-Phase Formation Process of Nitrated Polycyclic Aromatic Hydrocarbons in the Atmosphere: A Computational Study. Environmental Science & Technology, 48, 5051-5057. https://doi.org/10.1021/es500453g
[13]
Carissan, Y. and Klopper, W. (2010) Hydrogen Abstraction from Biphenyl, Acenaphthylene, Naphthalene and Phenanthrene by Atomic Hydrogen and Methyl Radical: DFT and G3 (MP2)-RAD Data. Journal of Molecular Structure: THEOCHEM, 940, 115-118.
https://doi.org/10.1016/j.theochem.2009.10.017
[14]
Lee, J. and Lane, D.A. (2010) Formation of Oxidized Products from the Reaction of Gaseous Phenanthrene with the OH Radical in a Reaction Chamber. Atmospheric Environment, 44, 2469-2477. https://doi.org/10.1016/j.atmosenv.2010.03.008
[15]
Kameda, T., Inazu, K., Asano, K., Murota, M., Takenaka, N., Sadanaga, Y., Hisamatsu, Y. and Bandow, H. (2013) Prediction of Rate Constants for the Gas Phase Reactions of Triphenylene with OH and NO3 Radicals Using a Relative Rate Method in CCl4 Liquid Phase-System. Chemosphere, 90, 766-771. https://doi.org/10.1016/j.chemosphere.2012.09.071
[16]
Dang, J., Shi, X.L., Zhang, Q.Z., Hu, J.T. and Wang, W.X. (2015) Mechanism and Kinetic Properties for the OH-Initiated Atmospheric Oxidation Degradation of 9, 10-Dichlorophenanthrene. Science of the Total Environment, 505, 787-794.
https://doi.org/10.1016/j.scitotenv.2014.10.081
[17]
Liu, C., Li, S.Q., Gao, R., Dang, J., Wang, W.X. and Zhang, Q.Z. (2014) Mechanism and Kinetic Properties of NO3-Initiated Atmospheric Degradation of DDT. Journal of Environmental Sciences, 26, 601-607. https://doi.org/10.1016/S1001-0742(13)60388-5
[18]
Dang, J., Shi, X.L., Zhang, Q.Z., Hu, J.T. and Wang, W.X. (2015) Mechanism and Thermal Rate Constant for the Gas-Phase Ozonolysis of Acenaphthylene in the Atmosphere. Science of the Total Environment, 514, 344-350. https://doi.org/10.1016/j.scitotenv.2014.12.009
[19]
Zhou, S. and Wenger, J.C. (2013) Kinetics and Products of the Gas-Phase Reactions of Acenaphthylene with Hydroxyl Radicals, Nitrate Radicals and Ozone. Atmospheric Environment, 75, 103-112. https://doi.org/10.1016/j.atmosenv.2013.04.049
[20]
Shiraiwa, M., Garland, R.M. and Poschl, U. (2009) Kinetic Double-Layer Model of Aerosol Surface Chemistry and Gas-Particle Interactions (K2-SURF): Degradation of Polycyclic Aromatic Hydrocarbons Exposed to O3, NO2, H2O, OH and NO3. Atmospheric Chemistry and Physics, 9, 9571-9586. https://doi.org/10.5194/acp-9-9571-2009
[21]
Atkinson, R. (2000) Atmospheric Chemistry of VOCs and NOx. Atmospheric. Environment, 34, 2063-2101. https://doi.org/10.1016/S1352-2310(99)00460-4
[22]
Reisen, F. and Arey, J. (2002) Reactions of Hydroxyl Radicals and Ozone with Acenaphthene and Acenaphthylene. Environmental Science & Technology, 36, 4302-4311.
https://doi.org/10.1021/es025761b
[23]
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., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A.J., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J. and Fox, D.J. (2009) Gaussian 09, Revision A.02. Gaussian, Inc., Wallingford.
[24]
Zhao, Y. and Truhalr, D.G. (2008) The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals. Theoretical Chemistry Accounts, 120, 215-241.
https://doi.org/10.1007/s00214-007-0310-x
[25]
Priya, A.M. and Senthilkumar, L. (2015) Reaction of OH Radical and Ozone with Methyl Salicylate—A DFT Study. Journal of Physical Organic Chemistry, 28, 542-553.
https://doi.org/10.1002/poc.3447
[26]
Sandhiya, L., Kolandaivel, P. and Senthilkumar, K. (2013) Mechanism and Kinetics of the Atmospheric Oxidative Degradation of Dimethylphenol Isomers Initiated by OH Radical. The Journal of Physical Chemistry A, 117, 4611-4626. https://doi.org/10.1021/jp3120868
