Hydrogen-Abstraction/Acetylene-Addition Exposed

Yang, Tao; Troy, Tyler P.; Xu, Bo; Kostko, Oleg; Ahmed, Musahid; Mebel, Alexander M.; Kaiser, Ralf I.

doi:10.1002/anie.201607509

Title: Hydrogen-Abstraction/Acetylene-Addition Exposed

Journal Article · Wed Oct 26 00:00:00 EDT 2016 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.201607509· OSTI ID:1464134

^[1]; Troy, Tyler P. ^[2]; Xu, Bo ^[2];

^[2]; Ahmed, Musahid ^[2]; Mebel, Alexander M. ^[3];

^[1]

Univ. of Hawaii at Manoa, Honolulu, HI (United States). Dept. of Chemistry
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Chemical Sciences Division
Florida Intl Univ., Miami, FL (United States). Dept. of Chemistry and Biochemistry

Polycyclic aromatic hydrocarbons (PAHs) are omnipresent in the interstellar medium (ISM) and also in carbonaceous meteorites (CM) such as Murchison. However, the basic reaction routes leading to the formation of even the simplest PAH—naphthalene (C₁₀H₈)—via the hydrogen-abstraction/acetylene-addition (HACA) mechanism still remain ambiguous. By revealing the uncharted fundamental chemistry of the styrenyl (C₈H₇) and the ortho-vinylphenyl radicals (C₈H₇)—key transient species of the HACA mechanism—with acetylene (C₂H₂), we provide the first solid experimental evidence on the facile formation of naphthalene in a simulated combustion environment validating the previously postulated HACA mechanism for these two radicals. This study highlights, at the molecular level spanning combustion and astrochemistry, the importance of the HACA mechanism to the formation of the prototype PAH naphthalene.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States); Univ. of Hawaii at Manoa, Honolulu, HI (United States); Florida International Univ. (FIU), Miami, FL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division

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

OSTI ID:: 1464134

Alternate ID(s):: OSTI ID: 1602921

Journal Information:: Angewandte Chemie (International Edition), Vol. 55, Issue 48; Related Information: © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 45 works

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Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition–Dehydrocyclization: The Third Way Zhao, Long; Prendergast, Matthew B.; Kaiser, Ralf I. Angewandte Chemie, Vol. 131, Issue 48 https://doi.org/10.1002/ange.201909876	journal	November 2019
Synthesis of Polycyclic Aromatic Hydrocarbons by Phenyl Addition-Dehydrocyclization: The Third Way Zhao, Long; Prendergast, Matthew B.; Kaiser, Ralf I. Angewandte Chemie International Edition, Vol. 58, Issue 48 https://doi.org/10.1002/anie.201909876	journal	October 2019
Molecular mass growth through ring expansion in polycyclic aromatic hydrocarbons via radical–radical reactions Zhao, Long; Kaiser, Ralf. I.; Lu, Wenchao Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-11652-5	journal	August 2019
Polycyclic aromatic hydrocarbon formation chemistry in a plasma jet revealed by IR-UV action spectroscopy Lemmens, Alexander K.; Rap, Daniël B.; Thunnissen, Johannes M. M. Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-019-14092-3	journal	January 2020
Low-temperature formation of polycyclic aromatic hydrocarbons in Titan’s atmosphere Zhao, Long; Kaiser, Ralf I.; Xu, Bo Nature Astronomy, Vol. 2, Issue 12 https://doi.org/10.1038/s41550-018-0585-y	journal	October 2018
From benzene to naphthalene: direct measurement of reactions and intermediates of phenyl radicals and acetylene Chu, Te-Chun; Buras, Zachary J.; Smith, Mica C. Physical Chemistry Chemical Physics, Vol. 21, Issue 40 https://doi.org/10.1039/c9cp04554f	journal	January 2019
Application of High-Resolution NMR and GC–MS to Study Hydrocarbon Oils Derived from Noncatalytic Thermal Transformation of e-Waste Plastics Kumar, Uttam; Gaikwad, Vaibhav; Mayyas, Mohannad ACS Omega, Vol. 3, Issue 8 https://doi.org/10.1021/acsomega.8b01284	journal	August 2018

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