Unconventional gas-phase preparation of the prototype polycyclic aromatic hydrocarbon naphthalene (C 10 H 8 ) via the reaction of benzyl (C 7 H 7 ) and propargyl (C 3 H 3 ) radicals coupled with hydrogen-atom assisted isomerization

He, Chao; Kaiser, Ralf I.; Lu, Wenchao; Ahmed, Musahid; Krasnoukhov, Vladislav S.; Pivovarov, Pavel S.; Zagidullin, Marsel V.; Azyazov, Valeriy N.; Morozov, Alexander N.; Mebel, Alexander M.

doi:10.1039/D3SC00911D

Title: Unconventional gas-phase preparation of the prototype polycyclic aromatic hydrocarbon naphthalene (C ₁₀ H ₈ ) via the reaction of benzyl (C ₇ H ₇ ) and propargyl (C ₃ H ₃ ) radicals coupled with hydrogen-atom assisted isomerization

Journal Article · Wed May 24 00:00:00 EDT 2023 · Chemical Science

DOI:https://doi.org/10.1039/D3SC00911D· OSTI ID:1972235

^[1];

^[2];

^[2]; Krasnoukhov, Vladislav S. ^[3]; Pivovarov, Pavel S. ^[4]; Zagidullin, Marsel V. ^[5];

^[5]; Morozov, Alexander N. ^[6];

^[6]

Department of Chemistry, University of Hawai'i at Mānoa, Honolulu, HI 96822, USA
Chemical Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720, USA
Lebedev Physical Institute, Samara 443011, Russian Federation, Samara National Research University, Samara 443086, Russian Federation
Samara National Research University, Samara 443086, Russian Federation
Lebedev Physical Institute, Samara 443011, Russian Federation
Department of Chemistry and Biochemistry, Florida International University, Miami, Florida 33199, USA

Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous in the interstellar medium and in meteorites such as Murchison and Allende and signify the missing link between resonantly stabilized free radicals and carbonaceous nanoparticles (soot particles, interstellar grains). However, the predicted lifetime of interstellar PAHs of some 108 years imply that PAHs should not exist in extraterrestrial environments suggesting that key mechanisms of their formation are elusive. Exploiting a microchemical reactor and coupling these data with computational fluid dynamics (CFD) simulations and kinetic modeling, we reveal through an isomer selective product detection that the reaction of the resonantly stabilized benzyl (C₇H₇) and the propargyl (C₃H₃) synthesizes the simplest representative of PAHs – the 10π Hückel aromatic naphthalene (C₁₀H₈) molecule – via the novel Propargyl Addition–BenzAnnulation (PABA) mechanism. The gas-phase preparation of naphthalene affords a versatile concept of the reaction of combustion and astronomically abundant propargyl radicals with aromatic radicals carrying the radical center at the methylene moiety (aromatic-CH₂) as a previously passed over source of aromatics in high temperature environments thus bringing us closer to an understanding of the aromatic universe we live in.

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Research Organization:: Univ. of Hawaii, Honolulu, HI (United States); Florida International Univ. (FIU), Miami, FL (United States); Advanced Light Source

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); Ministry of Higher Education and Science of the Russian Federation

Grant/Contract Number:: AC02-05CH11231; FG02-03ER15411; FG02-04ER15570; 075-15-2021-597

OSTI ID:: 1972235

Alternate ID(s):: OSTI ID: 1975327

Journal Information:: Chemical Science, Journal Name: Chemical Science Vol. 14 Journal Issue: 20; ISSN 2041-6520

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

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Title: Unconventional gas-phase preparation of the prototype polycyclic aromatic hydrocarbon naphthalene (C 10 H 8 ) via the reaction of benzyl (C 7 H 7 ) and propargyl (C 3 H 3 ) radicals coupled with hydrogen-atom assisted isomerization

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Title: Unconventional gas-phase preparation of the prototype polycyclic aromatic hydrocarbon naphthalene (C ₁₀ H ₈ ) via the reaction of benzyl (C ₇ H ₇ ) and propargyl (C ₃ H ₃ ) radicals coupled with hydrogen-atom assisted isomerization