Formation of 5- and 6-methyl-1H-indene (C10H10) via the reactions of the para-tolyl radical (C6H4CH3) with allene (H2CCCH 2) and methylacetylene (HCCCH3) under single collision conditions

Yang, Tao; Parker, Dorian S.  N.; Dangi, Beni B.; Kaiser, Ralf I.; Mebel, Alexander M.

doi:10.1039/c4cp04288c

Formation of 5- and 6-methyl-1H-indene (C₁₀H₁₀) via the reactions of the para-tolyl radical (C₆H₄CH₃) with allene (H₂CCCH ₂) and methylacetylene (HCCCH₃) under single collision conditions

Journal Article · Mon Mar 02 23:00:00 EST 2015 · Physical Chemistry Chemical Physics. PCCP

DOI:https://doi.org/10.1039/c4cp04288c· OSTI ID:1602876

Yang, Tao ^[1]; Parker, Dorian S. N. ^[2]; Dangi, Beni B. ^[2]; Kaiser, Ralf I. ^[2]; Mebel, Alexander M. ^[3]

Univ. of Hawaii at Manoa, Honolulu, HI (United States); University of Hawaii at Manoa
Univ. of Hawaii at Manoa, Honolulu, HI (United States)
Florida International Univ., Miami, FL (United States)

The reactions of the p-tolyl radical with allene-d4 and methylacetylene-d4 as well as of the p-tolyl-d7 radical with methylacetylene-d1 and methylacetylene-d3 were carried out under single collision conditions at collision energies of 44–48 kJ mol^-1 and combined with electronic structure and statistical (RRKM) calculations. Our experimental results indicated that the reactions of p-tolyl with allene-d4 and methylacetylene-d4 proceeded via indirect reaction dynamics with laboratory angular distributions spanning about 20° in the scattering plane. As a result, the center-of-mass translational energy distribution determined a reaction exoergicity of 149 ± 28 kJ mol^-1 and exhibited a pronounced maximum at around 20 to 30 kJ mol^-1. In addition, the center-of-mass angular flux distribution T(θ) depicted a forward–backward symmetry and indicated geometric constraints upon the decomposing complex(es). Combining with calculations, these results propose that the bicyclic polycyclic aromatic hydrocarbons, 6-methyl-1H-indene (p1) and 5-methyl-1H-indene (p2), are formed under single collision conditions at fractions of at least 85% in both reaction systems. For the p-tolyl–methylacetylene system, experiments with partially deuterated reactants also reveal the formation of a third isomer p5 (1-methyl-4-(1-propynyl)benzene) at levels of 5–10%, highlighting the importance in conducting reactions with partially deuterated reactants to elucidate the underlying reaction pathways comprehensively.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Hawaii at Manoa, Honolulu, HI (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: FG02-03ER15411; FG02-04ER15570

OSTI ID:: 1602876

Journal Information:: Physical Chemistry Chemical Physics. PCCP, Journal Name: Physical Chemistry Chemical Physics. PCCP Journal Issue: 16 Vol. 17; ISSN 1463-9076; ISSN PPCPFQ

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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