Theoretical kinetic investigation of the multichannel mechanism of O(3P) atmospheric oxidation reaction of but-3-enal

Year 2024, , 38 - 47, 21.05.2024

Boulanouar Messaoudı , Mouna Cheriet , Rayanne Djemıl , Khatmi Djamel Eddine

https://doi.org/10.33435/tcandtc.1277724

Abstract

Several levels of theory such as Møller-Plesset MP2, G3, and CBS-QB3, have been used in order to investigate the complex and multichannel potential energy surface of the reaction of but-3-enal with the triplet oxygen atom. The results show that the O-addition channel is dominant. The different possible pathways of oxygen atom attack are thoroughly studied to better understand and explain the reaction mechanism. Regarding the oxidation of but-3-enal by triplet oxygen O(3P), it is shown that the major thermodynamic product is H3CC(O)CH2C(O)H (P3) being the most stable for the whole reaction. However, the most favored product kinetically is H2CC(OH)CH2C(O)H (P2). For the H-abstraction second possible pathway, the most favored product both kinetically and thermodynamically is found to be P8. The activation energy and calculated rate constants are consistent with the proposed addition mechanism.

Keywords

But-3-enal, O(3P), G3 method, O-addition, H-abstraction.

References

• [1] R. Atkinson, "Gas-phase tropospheric chemistry of organic compounds: a review," Atmospheric Environment. Part A. General Topics, 24 (1990) 1-41.
• [2] B. J. Finlayson-Pitts, J. N. Pitts Jr, "Chemistry of the upper and lower atmosphere" San Diego, CA: Academic (2000).
• [3] A. Caracciolo, G. Vanuzzo, N. Balucani, et al., "Combined experimental and theoretical studies of the O(3P)+ 1-butene reaction dynamics: Primary products, branching fractions, and role of intersystem crossing," The Journal of Physical Chemistry A, 123 (2019) 9934-9956.
• [4] C. Cavallotti, A. Della Libera, C. W. Zhou, et al., "Crossed-beam and theoretical studies of multichannel nonadiabatic reactions: branching fractions and role of intersystem crossing for O(3P) + 1,3-butadiene," Faraday Discussions, 238 (2022) 161-182.
• [5] J. F. Alarcon, A. M. Mebel, "Direct H abstraction by molecular oxygen from unsaturated C3–C5 hydrocarbons: A theoretical study," International Journal of Chemical Kinetics, 54 (2022) 203-217.
• [6] R. Quandt, M. Zhiyuan, W. Xuebin, et al., "Reactions of O(3P) with alkenes: H, CH2CHO, CO, and OH channels," The Journal of Physical Chemistry A, 102 (1998) 60-64.
• [7] S. Hirokami, R. J. Cvetanović, "Reaction of oxygen atoms, O(3P), with olefins in liquid nitrogen solution at 770K," Journal of the American Chemical Society, 96 (1974) 3738-3746.
• [8] T. Oguchi, I. Akira, K. Yukino et al., "Mechanism of the reactions of butenes with O(3P): the yields of CH3 and C2H5," The Journal of Physical Chemistry A, 108 (2004) 1409-1416.
• [9] Y. Ren, L. Zhou, A. Mellouki, et al., "Reactions of NO3 with aromatic aldehydes: gas-phase kinetics and insights into the mechanism of the reaction," Atmospheric Chemistry and Physics, 21 (2021) 13537-13551.
• [10] B. Long, Y. Xia, D. G. Truhlar, "Quantitative kinetics of HO2 reactions with aldehydes in the atmosphere: high-order dynamic correlation, anharmonicity, and falloff effects are All important," Journal of American Chemical Society, 144 (2022) 19910-19920.
• [11] C. N. Hewitt, "Reactive Hydrocarbons in the Atmosphere, Academic Press, (1998).
• [12] C.A. Taatjes, H. Nils, M. Andrew, et al., "Enols are common intermediates in hydrocarbon oxidation," Science, 308 (2005) 1887-1889.
• [13] Z. Min, W. Teh-Hwa, S. Hongmei, et al., "Reaction of O(3P) with alkenes: Side chain vs double bond attack," The Journal of Physical Chemistry A, 104 (2000) 9941-9943.
• [14] J. S. Gaffney, R. Atkinson, J. N. Pitts Jr., "Relative rate constants for the reaction of oxygen (3P) atoms with selected olefins, monoterpenes, and unsaturated aldehydes," Journal of the American Chemical Society, 97 (1975) 5049-5051.
• [15] J. S. Gaffney, R. Atkinson, N. Pitts Jr. James, "Temperature dependence of the relative rate constants for the reaction of oxygen (3P) atoms with selected olefins, monoterpenes, and unsaturated aldehydes," Journal of the American Chemical Society, 97 (1975) 6481-6483.
• [16] M. Passos, L. Igor, V. Mateus, et al., "The 3-butenal+ H reactions: an application of the multipath canonical variational theory," Authorea Preprints, (2020).
• [17] R. Atkinson, M.A. Sara, N. Pitts Jr. James, "Kinetics of the gas‐phase reactions of OH radicals with a series of α, β‐unsaturated carbonyls at 299±2 K," International Journal of Chemical Kinetics, 15 (1983) 75-81.
• [18] R. Atkinson, "A structure‐activity relationship for the estimation of rate constants for the gas‐phase reactions of OH radicals with organic compounds," International Journal of Chemical Kinetics, 19 (1987) 799 828.
• [19] C. Papagni, A. Janet, R. Atkinson, "Rate constants for the gas‐phase reactions of a series of C3- C6 aldehydes with OH and NO3 radicals," International Journal of Chemical Kinetics, 32 (2000) 79-84.
• [20] R. Atkinson, M. A. Sara, M.W. Arthur, et al., "Rate constants for the gas‐phase reactions of O3 with a series of carbonyls at 296 K," International Journal of Chemical Kinetics, 13 (1981) 1133-1142.
• [21] D. Grosjean, E. Grosjean, E. L. Williams, "Rate constants for the gas‐phase reactions of ozone with unsaturated alcohols, esters, and carbonyls," International Journal of Chemical Kinetics, 25 (1993) 783-794.
• [22] P. Pechukas, "Transition state theory," Annual Review of Physical Chemistry, 32 (1981) 159-177.
• [23] B. L. Foley, A. Bhan, "Degree of rate control and De Donder relations–An interpretation based on transition state theory," Journal of Catalysis, 384 (2020) 231-251.
• [24] a) K. Han, T. Chi, "Reaction rate constant computations: theories and applications (Vol. 6)," Royal Society of Chemistry, (2014). b) B. Peters, "Reaction rate theory and rare events," Elsevier, (2017).
• [25] M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al., Gaussian 09, Inc., Wallingford CT, 2009.
• [26] M. Head-Gordon, J. A. Pople, M. J. Frisch, "MP2 energy evaluation by direct methods," Chemical Physics Letters, 153 (1988) 503-506.
• [27] L. A. Curtiss, R. Krishnan, C. R. Paul, et al., "Gaussian-3 (G3) theory for molecules containing first and second-row atoms," The Journal of Chemical Physics, 109 (1998) 7764-7776.
• [28] L. A. Curtiss, R. Krishnan, "Gaussian-3 and related methods for accurate thermochemistry," Theoretical Chemistry Accounts, 108 (2002) 61-70.
• [29] G. A. Petersson, T. G. Tensfeldt, J. A. Montgomery Jr., "A complete basis set model chemistry. III. The complete basis set-quadratic configuration interaction family of methods," Journal of Chemical Physics, 94 (1991) 6091-6101.
• [30] J. W. Ochterski, G. A. Petersson, J. A. Montgomery Jr., "A complete basis set model chemistry. V. Extensions to six or more heavy atoms," Journal of Chemical Physics, 104 (1996) 2598-2619.
• [31] C. Gonzalez, H. B. Schlegel, "Reaction path following in mass-weighted internal coordinates," Journal of Physical Chemistry, 94 (1990) 5523-5527.
• [32] D. L. Singleton, R. J. Cvetanović, "Temperature dependence of the reaction of oxygen atoms with olefins," Journal of the American Chemical Society, 98 (1976) 6812-6819.
• [33] S. Canneaux, F. Bohr, E. Henon, "KiSThelP: a program to predict thermodynamic properties and rate constants from quantum chemistry results," Journal of Computational Chemistry, 35 (2014) 82-93.
• [34] H. Khartabil, L. Doudet, I. Allart-Simon, et al., "Mechanistic insights into Smiles rearrangement. Focus on π–π stacking interactions along the radical cascade," Organic & Biomolecular Chemistry, 18 (2020) 6840-6848.
• [35] J. Dang, S. Tian, Q. Zhang, "Mechanism and kinetics studies of the atmospheric oxidation of p, p'-Dicofol by OH and NO3 radicals," Chemosphere, 219 (2019) 645-654.
• [36] G. Y. Adusei, A. Fontijn, "Kinetics of the reaction between oxygen (3P) atoms and 1, 3-butadiene between 280 and 1015 K," The Journal of Physical Chemistry, 97 (1993) 1406-1408.