HACA's Heritage: A Free-Radical Pathway to Phenanthrene in Circumstellar Envelopes of Asymptotic Giant Branch Stars

Yang, Tao; Kaiser, Ralf I.; Troy, Tyler P.; Xu, Bo; Kostko, Oleg; Ahmed, Musahid; Mebel, Alexander M.; Zagidullin, Marsel V.; Azyazov, Valeriy N.

doi:10.1002/anie.201701259

HACA's Heritage: A Free-Radical Pathway to Phenanthrene in Circumstellar Envelopes of Asymptotic Giant Branch Stars

Journal Article · Wed Mar 22 00:00:00 EDT 2017 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.201701259· OSTI ID:1464146

^[1]; ^[1]; Troy, Tyler P. ^[2]; Xu, Bo ^[2]; ^[2]; ^[2]; Mebel, Alexander M. ^[3]; Zagidullin, Marsel V. ^[4]; Azyazov, Valeriy N. ^[4]

Univ. of Hawaii, 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
Samara National Research Univ. (Russian Federation). Dept. of Physics

The hydrogen-abstraction/acetylene-addition (HACA) mechanism has been central for the last decades in attempting to rationalize the formation of polycyclic aromatic hydrocarbons (PAHs) as detected in carbonaceous meteorites such as in Murchison. Nevertheless, the basic reaction mechanisms leading to the formation of even the simplest tricyclic PAHs like anthracene and phenanthrene are still elusive. By exploring the previously unknown chemistry of the ortho-biphenylyl radical with acetylene, we deliver compelling evidence on the efficient synthesis of phenanthrene in carbon-rich circumstellar environments. However, the lack of formation of the anthracene isomer implies that HACA alone cannot be responsible for the formation of PAHs in extreme environments. Considering the overall picture, alternative pathways such as vinylacetylene-mediated reactions are required to play a crucial role in the synthesis of complex PAHs in circumstellar envelopes of dying carbon-rich stars.

View Accepted Manuscript (DOE)

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

Sponsoring Organization:: Government of the Russian Federation; USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division

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

OSTI ID:: 1464146

Alternate ID(s):: OSTI ID: 1602963
OSTI ID: 1376753

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 16 Vol. 56; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

References (44)

Hydrogen Abstraction/Acetylene Addition Revealed Parker, Dorian S. N.; Kaiser, Ralf I.; Troy, Tyler P. Angewandte Chemie, Vol. 126, Issue 30 https://doi.org/10.1002/ange.201404537	journal	June 2014
Unexpected Chemistry from the Reaction of Naphthyl and Acetylene at Combustion-Like Temperatures Parker, Dorian S. N.; Kaiser, Ralf. I.; Bandyopadhyay, Biswajit Angewandte Chemie, Vol. 127, Issue 18 https://doi.org/10.1002/ange.201411987	journal	March 2015
Hydrogen-Abstraction/Acetylene-Addition Exposed Yang, Tao; Troy, Tyler P.; Xu, Bo Angewandte Chemie, Vol. 128, Issue 48 https://doi.org/10.1002/ange.201607509	journal	October 2016
Hydrogen Abstraction/Acetylene Addition Revealed Parker, Dorian S. N.; Kaiser, Ralf I.; Troy, Tyler P. Angewandte Chemie International Edition, Vol. 53, Issue 30 https://doi.org/10.1002/anie.201404537	journal	June 2014
Unexpected Chemistry from the Reaction of Naphthyl and Acetylene at Combustion-Like Temperatures Parker, Dorian S. N.; Kaiser, Ralf. I.; Bandyopadhyay, Biswajit Angewandte Chemie International Edition, Vol. 54, Issue 18 https://doi.org/10.1002/anie.201411987	journal	March 2015
Hydrogen-Abstraction/Acetylene-Addition Exposed Yang, Tao; Troy, Tyler P.; Xu, Bo Angewandte Chemie International Edition, Vol. 55, Issue 48 https://doi.org/10.1002/anie.201607509	journal	October 2016
Computational study on the recombination reaction between benzyl and propargyl radicals Matsugi, Akira; Miyoshi, Akira International Journal of Chemical Kinetics, Vol. 44, Issue 3 https://doi.org/10.1002/kin.20625	journal	January 2012
Polycyclic aromatic hydrocarbons in the Murchison meteorite Basile, Brenda P.; Middleditch, Brian S.; Oró, J. Organic Geochemistry, Vol. 5, Issue 4 https://doi.org/10.1016/0146-6380(84)90008-1	journal	January 1984
A detailed kinetic modeling study of aromatics formation in laminar premixed acetylene and ethylene flames Wang, Hai; Frenklach, Michael Combustion and Flame, Vol. 110, Issue 1-2 https://doi.org/10.1016/S0010-2180(97)00068-0	journal	July 1997
Kinetic modeling of soot formation with detailed chemistry and physics: laminar premixed flames of C2 hydrocarbons Appel, Jörg; Bockhorn, Henning; Frenklach, Michael Combustion and Flame, Vol. 121, Issue 1-2 https://doi.org/10.1016/S0010-2180(99)00135-2	journal	April 2000
Formation pathways of ethynyl-substituted and cyclopenta-fused polycyclic aromatic hydrocarbons Marsh, Nathan D.; Wornat, Mary J. Proceedings of the Combustion Institute, Vol. 28, Issue 2 https://doi.org/10.1016/S0082-0784(00)80676-1	journal	January 2000
Spectroscopic properties of polycyclic aromatic hydrocarbons (PAHs) and astrophysical implications d'Hendecourt, L.; Ehrenfreund, P. Advances in Space Research, Vol. 19, Issue 7 https://doi.org/10.1016/S0273-1177(97)00349-9	journal	January 1997
Formation of polycyclic aromatic hydrocarbons and their growth to soot—a review of chemical reaction pathways Richter, H.; Howard, J. B. Progress in Energy and Combustion Science, Vol. 26, Issue 4-6 https://doi.org/10.1016/S0360-1285(00)00009-5	journal	August 2000
A novel route for PAH growth in HACA based mechanisms Shukla, Bikau; Koshi, Mitsuo Combustion and Flame, Vol. 159, Issue 12 https://doi.org/10.1016/j.combustflame.2012.08.007	journal	December 2012
On the kinetics of the C5H5+C5H5 reaction Cavallotti, Carlo; Polino, Daniela Proceedings of the Combustion Institute, Vol. 34, Issue 1 https://doi.org/10.1016/j.proci.2012.05.097	journal	January 2013
Temperature- and pressure-dependent rate coefficients for the HACA pathways from benzene to naphthalene Mebel, Alexander M.; Georgievskii, Yuri; Jasper, Ahren W. Proceedings of the Combustion Institute, Vol. 36, Issue 1 https://doi.org/10.1016/j.proci.2016.07.013	journal	January 2017
Interstellar and Circumstellar PAHs Tielens, A. G. G. M.; van Kerckhoven, C.; Peeters, E. Symposium - International Astronomical Union, Vol. 197 https://doi.org/10.1017/S0074180900164939	journal	January 2000
Astrochemistry: From Molecular Clouds to Planetary Systems; Conference Summary Williams, D. A. Symposium - International Astronomical Union, Vol. 197 https://doi.org/10.1017/S0074180900165106	journal	January 2000
Hydrogen Abstraction Acetylene Addition and Diels−Alder Mechanisms of PAH Formation: A Detailed Study Using First Principles Calculations Kislov, V. V.; Islamova, N. I.; Kolker, A. M. Journal of Chemical Theory and Computation, Vol. 1, Issue 5 https://doi.org/10.1021/ct0500491	journal	September 2005
Calculations of Rate Coefficients for the Chemically Activated Reactions of Acetylene with Vinylic and Aromatic Radicals Wang, Hai; Frenklach, Michael The Journal of Physical Chemistry, Vol. 98, Issue 44 https://doi.org/10.1021/j100095a033	journal	November 1994
Time-dependent mass spectra and breakdown graphs. 17. Naphthalene and phenanthrene Gotkis, Yehiel; Oleinikova, Maria; Naor, Mor The Journal of Physical Chemistry, Vol. 97, Issue 47 https://doi.org/10.1021/j100149a031	journal	November 1993
Reaction of Phenyl Radicals with Acetylene: Quantum Chemical Investigation of the Mechanism and Master Equation Analysis of the Kinetics Tokmakov, I. V.; Lin, M. C. Journal of the American Chemical Society, Vol. 125, Issue 37 https://doi.org/10.1021/ja0301121	journal	September 2003
Ab Initio and DFT Study of the Formation Mechanisms of Polycyclic Aromatic Hydrocarbons: The Phenanthrene Synthesis from Biphenyl and Naphthalene Kislov, V. V.; Mebel, A. M.; Lin, S. H. The Journal of Physical Chemistry A, Vol. 106, Issue 25 https://doi.org/10.1021/jp020406t	journal	June 2002
The Formation of Naphthalene, Azulene, and Fulvalene from Cyclic C ₅ Species in Combustion: An Ab Initio/RRKM Study of 9-H-Fulvalenyl (C ₅ H ₅ −C ₅ H ₄ ) Radical Rearrangements ^† Kislov, V. V.; Mebel, A. M. The Journal of Physical Chemistry A, Vol. 111, Issue 38 https://doi.org/10.1021/jp0732099	journal	September 2007
Formation Mechanism of Polycyclic Aromatic Hydrocarbons beyond the Second Aromatic Ring Kislov, V. V.; Sadovnikov, A. I.; Mebel, A. M. The Journal of Physical Chemistry A, Vol. 117, Issue 23 https://doi.org/10.1021/jp402481y	journal	May 2013
Reaction mechanism of soot formation in flames Frenklach, Michael Physical Chemistry Chemical Physics, Vol. 4, Issue 11 https://doi.org/10.1039/b110045a	journal	February 2002
Polycyclic aromatic hydrocarbons, carbon nanoparticles and the diffuse interstellar bands Duley, W. W. Faraday Discussions, Vol. 133 https://doi.org/10.1039/b516323d	journal	January 2006
Carbon molecules in space: from astrochemistry to astrobiology Ehrenfreund, Pascale; Sephton, Mark A. Faraday Discussions, Vol. 133 https://doi.org/10.1039/b517676j	journal	January 2006
A highly efficient growth mechanism of polycyclic aromatic hydrocarbons Shukla, Bikau; Koshi, Mitsuo Physical Chemistry Chemical Physics, Vol. 12, Issue 10 https://doi.org/10.1039/b919644g	journal	January 2010
Formation of the diphenyl molecule in the crossed beam reaction of phenyl radicals with benzene Zhang, Fangtong; Gu, Xibin; Kaiser, Ralf I. The Journal of Chemical Physics, Vol. 128, Issue 8 https://doi.org/10.1063/1.2834221	journal	February 2008
The chemistry in circumstellar envelopes of evolved stars: Following the origin of the elements to the origin of life Ziurys, L. M. Proceedings of the National Academy of Sciences, Vol. 103, Issue 33 https://doi.org/10.1073/pnas.0602277103	journal	August 2006
Charged polycyclic aromatic hydrocarbon clusters and the galactic extended red emission Rhee, Y. M.; Lee, T. J.; Gudipati, M. S. Proceedings of the National Academy of Sciences, Vol. 104, Issue 13 https://doi.org/10.1073/pnas.0609396104	journal	March 2007
High molecular diversity of extraterrestrial organic matter in Murchison meteorite revealed 40 years after its fall Schmitt-Kopplin, P.; Gabelica, Z.; Gougeon, R. D. Proceedings of the National Academy of Sciences, Vol. 107, Issue 7 https://doi.org/10.1073/pnas.0912157107	journal	February 2010
Low temperature formation of naphthalene and its role in the synthesis of PAHs (Polycyclic Aromatic Hydrocarbons) in the interstellar medium Parker, D. S. N.; Zhang, F.; Kim, Y. S. Proceedings of the National Academy of Sciences, Vol. 109, Issue 1 https://doi.org/10.1073/pnas.1113827108	journal	December 2011
Formation of polycyclic aromatic hydrocarbons in circumstellar envelopes Frenklach, Michael; Feigelson, Eric D. The Astrophysical Journal, Vol. 341 https://doi.org/10.1086/167501	journal	June 1989
Polycyclic aromatic hydrocarbon formation in carbon-rich stellar envelopes Cherchneff, Isabelle; Barker, John R.; Tielens, Alexander G. G. M. The Astrophysical Journal, Vol. 401 https://doi.org/10.1086/172059	journal	December 1992
Detection and Characterization of Cold Interstellar Dust and Polycyclic Aromatic Hydrocarbon Emission, from COBE Observations Dwek, E.; Arendt, R. G.; Fixsen, D. J. The Astrophysical Journal, Vol. 475, Issue 2 https://doi.org/10.1086/303568	journal	February 1997
Polycyclic Aromatic Hydrocarbons and the Diffuse Interstellar Bands: A Survey Salama, F.; Galazutdinov, G. A.; Krełowski, J. The Astrophysical Journal, Vol. 526, Issue 1 https://doi.org/10.1086/307978	journal	November 1999
The Infrared Spectrum of Protonated Naphthalene and its Relevance for the Unidentified Infrared Bands Ricks, Allen M.; Douberly, Gary E.; Duncan, Michael A. The Astrophysical Journal, Vol. 702, Issue 1 https://doi.org/10.1088/0004-637X/702/1/301	journal	August 2009
Aromatic Hydrocarbons in the Murchison Meteorite Pering, K. L.; Ponnamperuma, C. Science, Vol. 173, Issue 3993 https://doi.org/10.1126/science.173.3993.237	journal	July 1971
Complex Organic Interstellar Molecules Herbst, Eric; van Dishoeck, Ewine F. Annual Review of Astronomy and Astrophysics, Vol. 47, Issue 1 https://doi.org/10.1146/annurev-astro-082708-101654	journal	September 2009
Reaction Dynamics in Astrochemistry: Low-Temperature Pathways to Polycyclic Aromatic Hydrocarbons in the Interstellar Medium Kaiser, Ralf I.; Parker, Dorian S. N.; Mebel, Alexander M. Annual Review of Physical Chemistry, Vol. 66, Issue 1 https://doi.org/10.1146/annurev-physchem-040214-121502	journal	April 2015
A New Component of the Interstellar Matter: Small Grains and Large Aromatic Molecules Puget, J. L.; Léger, A. Annual Review of Astronomy and Astrophysics, Vol. 27, Issue 1 https://doi.org/10.1146/annurev.aa.27.090189.001113	journal	September 1989
Interstellar Polycyclic Aromatic Hydrocarbon Molecules Tielens, A. G. G. M. Annual Review of Astronomy and Astrophysics, Vol. 46, Issue 1 https://doi.org/10.1146/annurev.astro.46.060407.145211	journal	September 2008

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HACA's Heritage: A Free‐Radical Pathway to Phenanthrene in Circumstellar Envelopes of Asymptotic Giant Branch Stars

Journal Article · Tue Mar 21 20:00:00 EDT 2017 · Angewandte Chemie · OSTI ID:1377931

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
79 ASTRONOMY AND ASTROPHYSICS
circumstellar envelopes
gas phase chemistry
hydrogen-abstraction/acetylene-addition (HACA)
mass spectrometry
polycyclic aromatic hydrocarbons

HACA's Heritage: A Free-Radical Pathway to Phenanthrene in Circumstellar Envelopes of Asymptotic Giant Branch Stars

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