Scission of the Five-Membered Ring in 1-H-Inden-1-one C9H6O and Indenyl C9H7 in the Reactions with H and O Atoms

Ghildina, A. R.; Porfiriev, D. P.; Azyazov, V. N.; Mebel, A. M.

doi:10.1021/acs.jpca.9b04578

Title: Scission of the Five-Membered Ring in 1-H-Inden-1-one C₉H₆O and Indenyl C₉H₇ in the Reactions with H and O Atoms

Journal Article · 13 June 2019 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI: https://doi.org/10.1021/acs.jpca.9b04578 · OSTI ID:1594749

Ghildina, A. R. ^[1]; Porfiriev, D. P. ^[1]; Azyazov, V. N. ^[1];

^[2]

Samara Univ. (Russia); Lebedev Physical Inst., Samara (Russia)
Samara Univ. (Russia); Florida International Univ., Miami, FL (United States)

Quantum chemical G3(MP2,CC)//B3LYP/6-311G(d,p) calculations of the C₉H₇O potential energy surface were utilized to investigate the mechanism of the 1-H-inden-1-one (C₉H₆O) + H and indenyl (C₉H₇) + O reactions and were combined with Rice–Ramsperger–Kassel–Marcus Master Equation (RRKM-ME) calculations to predict temperature- and pressure-dependent reaction rate constants and product branching ratios. The most favorable reaction pathways for C₉H₆O + H lead to the bimolecular C₈H₇ + CO products, which are slightly endothermic with respect to the reactants. The reaction begins with H addition to the ortho or meta C atoms in the five-membered ring, C₉H₆O + H → w2/w3, and then proceeds by isomerization to w1, (w3 →) w2 → w1. From thereon, the w1 → w9 → w8 → p1 and w2 → w8 → p1 pathways lead to ortho-vinyl phenyl + CO, whereas w1 → w10 → w11 → p2 and C₉H₆O + H → w10 → w11 → p2 produce styrenyl + CO. The results of the RRKM-ME calculations showed that only the well-skipping C₉H₆O + H → C₈H₇ (p1/p2) + CO mechanism is relevant under combustion conditions. A comparison with a smaller prototype 2,4-cyclopentadienone + H → C₄H₅ + CO reaction demonstrated that the H atom is a less efficient destroyer of a cyclopentadienone-like moiety when this moiety is linked to an aromatic or a PAH structure. The C₉H₇ + O reaction begins with highly exothermic barrierless addition of the oxygen atom to the radical site in the five-membered ring of indenyl producing w1 and then, the reaction mostly proceeds by β-scission in the five-membered ring, which may be preceded by H migration to w2 or w10, and completes by the CO loss forming the highly exothermic C₈H₇ radical products. Modified Arrhenius expressions for the rate constants of all reactions pertinent to the formation of C₈H₇ + CO from C₉H₆O + H, C₉H₇ + H, and unimolecular decomposition of benzopyranyl have been generated and suggested for combustion kinetic modeling. Furthermore, it is concluded that the oxidation reactions of a five-membered ring with atomic oxygen remain fast in the presence of attached or surrounding six-membered rings.

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Research Organization:: Florida International Univ. (FIU), Miami, FL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: FG02-04ER15570; 14.Y26.31.0020

OSTI ID:: 1594749

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Vol. 123, Issue 27; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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