Formation of Benzene and Naphthalene through Cyclopentadienyl-Mediated Radical–Radical Reactions

Kaiser, Ralf I.; Zhao, Long; Lu, Wenchao; Ahmed, Musahid; Zagidullin, Marsel V.; Azyazov, Valeriy N.; Mebel, Alexander M.

doi:10.1021/acs.jpclett.1c03733

Title: Formation of Benzene and Naphthalene through Cyclopentadienyl-Mediated Radical–Radical Reactions

Journal Article · 29 December 2021 · Journal of Physical Chemistry Letters

DOI: https://doi.org/10.1021/acs.jpclett.1c03733 · OSTI ID:1843970

^[1]; Zhao, Long ^[2];

^[3];

^[3]; Zagidullin, Marsel V. ^[4]; Azyazov, Valeriy N. ^[4];

^[5]

Univ. of Hawaii at Manoa, Honolulu, HI (United States); Florida International University
Univ. of Hawaii at Manoa, Honolulu, HI (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Russian Academy of Sciences (RAS), Samara (Russian Federation). P.N. Lebedev Physical Institute
Florida International Univ. (FIU), Miami, FL (United States)

Resonantly stabilized free radicals (RSFRs) have been contemplated as fundamental molecular building blocks and reactive intermediates in molecular mass growth processes leading to polycyclic aromatic hydrocarbons (PAHs) and carbonaceous nanoparticles on Earth and in deep space. Here, by combining molecular beams and computational fluid dynamics simulations, we provide compelling evidence on the formation of benzene via the cyclopentadienyl-methyl reaction and of naphthalene through the cyclopentadienyl self-reaction, respectively. These systems offer benchmarks for the conversion of a five-membered ring to the 6π-aromatic (benzene) and the generation of the simplest 10π-PAH (naphthalene) at elevated temperatures. These results uncover molecular mass growth processes from the “bottom up” via RSFRs in high temperature circumstellar environments and combustion systems expanding our fundamental knowledge of the organic, hydrocarbon chemistry in our universe.

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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); Ministry of Higher Education and Science of the Russian Federation

Grant/Contract Number:: FG02-04ER15570; FG02-03ER15411; AC02-05CH11231

OSTI ID:: 1843970

Journal Information:: Journal of Physical Chemistry Letters, Journal Name: Journal of Physical Chemistry Letters Journal Issue: 1 Vol. 13; ISSN 1948-7185

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Title: Formation of Benzene and Naphthalene through Cyclopentadienyl-Mediated Radical–Radical Reactions

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