First aromatic ring formation by the radical-chain reaction of vinylacetylene and propargyl

Hanfeng Jin, Lili Xing, Dapeng Liu, Junyu Hao, Jiuzhong Yang, Aamir Farooq

Research output: Contribution to journalArticlepeer-review

17 Scopus citations


Recent investigations illustrated that clustering of hydrocarbons by radical-chain reaction (CHRCR) mechanism provides key mechanistic steps for the rapid synthesis of polycyclic aromatic hydrocarbons (PAHs) and soot. Resonance-stabilized radicals (RSRs) play critical roles in this mechanism, and non-benzene first-ring species have attracted considerable attention as precursors of larger aromatic hydrocarbons. C7H7 RSRs, such as benzyl, tropyl, vinyl-cyclopentadienyl, are particularly stable and are thus quite important in the growth of PAHs. The addition of vinylacetylene to propargyl radical, a prototypical CHRCR reaction, provides a facile route to C7H7 RSRs. We have directly investigated the reaction of propargyl and vinylacetylene in isomer-resolved elementary experiments by synchrotron vacuum ultra-violet photoionization molecular beam mass spectrometry (SVUV-PI-MBMS). In good agreement with theoretical predictions, vinyl-cyclopentadienyl is found to be the major product of vinylacetylene and propargyl reaction while benzyl is minor. This work demonstrates a feasible CHRCR pathway, not proceeding through benzene, for PAH formation.
Original languageEnglish (US)
Pages (from-to)524-534
Number of pages11
JournalCombustion and Flame
StatePublished - Dec 1 2020


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