A combined crossed molecular beam and theoretical investigation of the reaction of the meta-tolyl radical with vinylacetylene – toward the formation of methylnaphthalenes

Yang, Tao; Muzangwa, Lloyd; Kaiser, Ralf I.; Jamal, Adeel; Morokuma, Keiji

doi:10.1039/c5cp03285g

Title: A combined crossed molecular beam and theoretical investigation of the reaction of the meta-tolyl radical with vinylacetylene – toward the formation of methylnaphthalenes

Journal Article · Fri Jul 17 00:00:00 EDT 2015 · Physical Chemistry Chemical Physics. PCCP

DOI:https://doi.org/10.1039/c5cp03285g· OSTI ID:1602913

Yang, Tao ^[1]; Muzangwa, Lloyd ^[1]; Kaiser, Ralf I. ^[1]; Jamal, Adeel ^[2]; Morokuma, Keiji ^[3]

Univ. of Hawaii at Manoa, Honolulu, HI (United States)
Kyoto Univ. (Japan). Fukui Inst. for Fundamental Chemistry
Kyoto Univ. (Japan). Fukui Inst. for Fundamental Chemistry; Emory Univ., Atlanta, GA (United States)

Crossed molecular beam experiments and electronic structure calculations on the reaction of the meta-tolyl radical with vinylacetylene were conducted to probe the formation of methyl-substituted naphthalene isomers. We present the compelling evidence that under single collision conditions 1- and 2-methylnaphthalene can be formed without an entrance barrier via indirect scattering dynamics through a bimolecular collision of two non-PAH reactants: the meta-tolyl radical and vinylacetylene. The electronic structure calculations, conducted at the UCCSD(T)-F12b/cc-pVDZ//UM06-2x/cc-pVTZ + ZPE(UM06-2x/cc-pVTZ) level of theory, reveal that this reaction is initiated by the barrierless addition of the meta-tolyl radical to the terminal vinyl carbon (C1) of vinylacetylene, via a van-der-Waals complex implying that this mechanism can play a key role in forming methyl-substituted PAHs in low temperature extreme environments such as the low temperature interstellar medium and hydrocarbon-rich atmospheres of planets and their moons in the outer solar system. The reaction mechanism, proposed from the C₁₁H₁₁ potential energy surface, involves a sequence of isomerizations involving hydrogen transfer and ring closure, followed by hydrogen dissociation, which eventually leads to 1- and 2-methylnaphthalene in an overall exoergic process.

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

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); US Air Force Office of Scientific Research (AFOSR)

Grant/Contract Number:: FG02-03ER15411; FA9550-10-1-0304; FA9550-12-1-0472

OSTI ID:: 1602913

Journal Information:: Physical Chemistry Chemical Physics. PCCP, Vol. 17, Issue 33; ISSN 1463-9076

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 18 works

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