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Title: Hydrogen-Abstraction/Acetylene-Addition Exposed

Abstract

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 (C 10H 8)—via the hydrogen-abstraction/acetylene-addition (HACA) mechanism still remain ambiguous. By revealing the uncharted fundamental chemistry of the styrenyl (C 8H 7) and the ortho-vinylphenyl radicals (C 8H 7)—key transient species of the HACA mechanism—with acetylene (C 2H 2), 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.

Authors:
ORCiD logo [1];  [2];  [2]; ORCiD logo [2];  [2];  [3]; ORCiD logo [1]
  1. Univ. of Hawaii at Manoa, Honolulu, HI (United States). Dept. of Chemistry
  2. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Chemical Sciences Division
  3. Florida Intl Univ., Miami, FL (United States). Dept. of Chemistry and Biochemistry
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division
OSTI Identifier:
1464134
Grant/Contract Number:  
AC02-05CH11231; FG02‐03ER15411; FG02‐04ER15570
Resource Type:
Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Name: Angewandte Chemie (International Edition); Journal Volume: 55; Journal Issue: 48; Related Information: © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim; Journal ID: ISSN 1433-7851
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 79 ASTRONOMY AND ASTROPHYSICS; combustion; gas-phase chemistry; hydrogen-abstraction/acetylene-addition (HACA); mass spectrometry; polycylic aromatic hydrocarbons

Citation Formats

Yang, Tao, Troy, Tyler P., Xu, Bo, Kostko, Oleg, Ahmed, Musahid, Mebel, Alexander M., and Kaiser, Ralf I. Hydrogen-Abstraction/Acetylene-Addition Exposed. United States: N. p., 2016. Web. doi:10.1002/anie.201607509.
Yang, Tao, Troy, Tyler P., Xu, Bo, Kostko, Oleg, Ahmed, Musahid, Mebel, Alexander M., & Kaiser, Ralf I. Hydrogen-Abstraction/Acetylene-Addition Exposed. United States. doi:10.1002/anie.201607509.
Yang, Tao, Troy, Tyler P., Xu, Bo, Kostko, Oleg, Ahmed, Musahid, Mebel, Alexander M., and Kaiser, Ralf I. Wed . "Hydrogen-Abstraction/Acetylene-Addition Exposed". United States. doi:10.1002/anie.201607509. https://www.osti.gov/servlets/purl/1464134.
@article{osti_1464134,
title = {Hydrogen-Abstraction/Acetylene-Addition Exposed},
author = {Yang, Tao and Troy, Tyler P. and Xu, Bo and Kostko, Oleg and Ahmed, Musahid and Mebel, Alexander M. and Kaiser, Ralf I.},
abstractNote = {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.},
doi = {10.1002/anie.201607509},
journal = {Angewandte Chemie (International Edition)},
number = 48,
volume = 55,
place = {United States},
year = {2016},
month = {10}
}

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