Formation of phenanthrenyl radicals via the reaction of acenaphthyl with acetylene

Savchenkova, Anna S.; Chechet, Ivan V.; Matveev, Sergey G.; Frenklach, Michael; Mebel, Alexander M.

doi:10.1016/j.proci.2020.06.347

Formation of phenanthrenyl radicals via the reaction of acenaphthyl with acetylene

Journal Article · Sat Sep 12 00:00:00 EDT 2020 · Proceedings of the Combustion Institute

DOI:https://doi.org/10.1016/j.proci.2020.06.347· OSTI ID:1766442

^[1]; ^[2]; Matveev, Sergey G. ^[2]; ^[3]; ^[4]

Samara National Research Univ. (Russia); Florida International University
Samara National Research Univ. (Russia)
Univ. of California, Berkeley, CA (United States)
Samara National Research Univ. (Russia); Florida International Univ., Miami, FL (United States)

Ab initio G3(MP2,CC)/B3LYP/6–31G** calculations of the potential energy surface for the reaction of 3-acenaphthyl radical with acetylene were combined with Rice-Ramsperger-Kassel-Marcus Master Equation calculations of the temperature- and pressure-dependent reaction rate constants and product branching ratios with the goal to examine the transformation of an edge five-membered ring into a six-membered one. The reaction mechanism has been shown to contain two stages: (1) the formation of 3-ethynylacenaphthylene + H in the 3-acenaphthyl + C₂H₂ reaction via acetylene addition to the radical site and an H loss, (2) the formation of the 1-phenanthrenyl radical in the 3-ethynylacenaphthylene + H reaction via H addition to the five-membered ring followed by the ring flip. The results of kinetic modeling show this pathway being faster than the pathway proposed earlier featuring the CCH chemisorption on the six-membered ring without involvement of the five-membered ring. A kinetic test demonstrated the dominance of the former pathway for the formation of pyrene from naphthalene. Here, it is expected that the new mechanism plays a major role in the transformation of five-membered rings on edges of PAH structures.

View Accepted Manuscript (DOE)

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

Sponsoring Organization:: Ministry of Science and Higher Education of the Russian Federation; USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: FG02-04ER15570

OSTI ID:: 1766442

Alternate ID(s):: OSTI ID: 1817922

Journal Information:: Proceedings of the Combustion Institute, Journal Name: Proceedings of the Combustion Institute Journal Issue: 1 Vol. 38; ISSN 1540-7489

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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