Gas Phase Synthesis of (Iso)Quinoline and Its Role in the Formation of Nucleobases in the Interstellar Medium

Parker, Dorian S.  N.; Kaiser, Ralf. I.; Kostko, Oleg; Troy, Tyler P.; Ahmed, Musahid; Mebel, Alexander M.; Tielens, Alexander G.  G.  M.

doi:10.1088/0004-637X/803/2/53

Gas Phase Synthesis of (Iso)Quinoline and Its Role in the Formation of Nucleobases in the Interstellar Medium

Journal Article · Tue Apr 14 00:00:00 EDT 2015 · The Astrophysical Journal (Online)

DOI:https://doi.org/10.1088/0004-637X/803/2/53· OSTI ID:1602877

Parker, Dorian S. N. ^[1]; Kaiser, Ralf. I. ^[2]; Kostko, Oleg ^[3]; Troy, Tyler P. ^[3]; Ahmed, Musahid ^[3]; Mebel, Alexander M. ^[4]; Tielens, Alexander G. G. M. ^[5]

Univ. of Hawaii at Manoa, Honolulu, HI (United States); University of Hawaii at Manoa
Univ. of Hawaii at Manoa, Honolulu, HI (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Florida International Univ., Miami, FL (United States)
Univ. of Leiden, Leiden (The Netherlands)

Nitrogen-substituted polycyclic aromatic hydrocarbons (NPAHs) have been proposed to play a key role in the astrochemical evolution of the interstellar medium, yet the formation mechanisms of even their simplest prototypes—quinoline and isoquinoline—remain elusive. Here, we reveal a novel concept that under high temperature conditions representing circumstellar envelopes of carbon stars, (iso)quinoline can be synthesized via the reaction of pyridyl radicals with two acetylene molecules. The facile gas phase formation of (iso)quinoline in circumstellar envelopes defines a hitherto elusive reaction class synthesizing aromatic structures with embedded nitrogen atoms that are essential building blocks in contemporary biological-structural motifs. Once ejected from circumstellar shells and incorporated into icy interstellar grains in cold molecular clouds, these NPAHs can be functionalized by photo processing forming nucleobase-type structures as sampled in the Murchison meteorite.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Hawaii at Manoa, Honolulu, HI (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: FG02-03ER15411

OSTI ID:: 1602877

Alternate ID(s):: OSTI ID: 22522505

Journal Information:: The Astrophysical Journal (Online), Journal Name: The Astrophysical Journal (Online) Journal Issue: 2 Vol. 803; ISSN 1538-4357

Publisher:: Institute of Physics (IOP)Copyright Statement

Country of Publication:: United States

Language:: English

References (40)

A Unified Mechanism for Abiotic Adenine and Purine Synthesis in Formamide Hudson, Jeremy S.; Eberle, Joseph F.; Vachhani, Raj H. Angewandte Chemie International Edition, Vol. 51, Issue 21 https://doi.org/10.1002/anie.201108907	journal	April 2012
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
Synthesis of Pyrimidines and Triazines in Ice: Implications for the Prebiotic Chemistry of Nucleobases Menor-Salván, César; Ruiz-Bermejo, Dra. Marta; Guzmán, Marcelo I. Chemistry - A European Journal, Vol. 15, Issue 17 https://doi.org/10.1002/chem.200802656	journal	April 2009
A New Route for the Prebiotic Synthesis of Nucleobases and Hydantoins in Water/Ice Solutions Involving the Photochemistry of Acetylene Menor-Salván, César; Marín-Yaseli, Margarita R. Chemistry - A European Journal, Vol. 19, Issue 20 https://doi.org/10.1002/chem.201204313	journal	March 2013
The Photodissociation of Pyridine at 193 nm Prather, Kimberly A.; Lee, Yuan T. Israel Journal of Chemistry, Vol. 34, Issue 1 https://doi.org/10.1002/ijch.199400008	journal	January 1994
Determination of absolute photoionization cross-sections of aromatics and aromatic derivatives Zhou, Zhongyue; Xie, Mingfeng; Wang, Zhandong Rapid Communications in Mass Spectrometry, Vol. 23, Issue 24 https://doi.org/10.1002/rcm.4339	journal	December 2009
A Computational Study of the Mechanisms for the Incorporation of a Nitrogen Atom into Polycyclic Aromatic Hydrocarbons in the Titan Haze Ricca, A. Icarus, Vol. 154, Issue 2 https://doi.org/10.1006/icar.2001.6694	journal	December 2001
Basic nitrogen-heterocyclic compounds in the Murchison meteorite Stoks, Peter G.; Schwartz, Alan W. Geochimica et Cosmochimica Acta, Vol. 46, Issue 3 https://doi.org/10.1016/0016-7037(82)90222-8	journal	March 1982
Gaussian-3 theory using coupled cluster energies Curtiss, Larry A.; Raghavachari, Krishnan; Redfern, Paul C. Chemical Physics Letters, Vol. 314, Issue 1-2 https://doi.org/10.1016/S0009-2614(99)01126-4	journal	November 1999
Evidence that polycyclic aromatic hydrocarbons in two carbonaceous chondrites predate parent-body formation Plows, Fiona L.; Elsila, Jamie E.; Zare, Richard N. Geochimica et Cosmochimica Acta, Vol. 67, Issue 7 https://doi.org/10.1016/S0016-7037(02)01277-2	journal	April 2003
Detailed modeling of soot particle nucleation and growth Frenklach, Michael; Wang, Hai Symposium (International) on Combustion, Vol. 23, Issue 1 https://doi.org/10.1016/S0082-0784(06)80426-1	journal	January 1991
Composition profiles and reaction mechanisms in a near-sooting premixed benzene/oxygen/argon flame Bittner, J. D.; Howard, J. B. Symposium (International) on Combustion, Vol. 18, Issue 1 https://doi.org/10.1016/S0082-0784(81)80115-4	journal	January 1981
The deuterium enrichment of individual amino acids in carbonaceous meteorites: A case for the presolar distribution of biomolecule precursors Pizzarello, Sandra; Huang, Yongsong Geochimica et Cosmochimica Acta, Vol. 69, Issue 3 https://doi.org/10.1016/j.gca.2004.07.031	journal	February 2005
Nitrogen-containing compounds in two CR2 meteorites: 15N composition, molecular distribution and precursor molecules Pizzarello, Sandra; Holmes, William Geochimica et Cosmochimica Acta, Vol. 73, Issue 7 https://doi.org/10.1016/j.gca.2009.01.022	journal	April 2009
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
PAH Formation under Single Collision Conditions: Reaction of Phenyl Radical and 1,3-Butadiene to Form 1,4-Dihydronaphthalene Kaiser, R. I.; Parker, D. S. N.; Zhang, F. The Journal of Physical Chemistry A, Vol. 116, Issue 17 https://doi.org/10.1021/jp301775z	journal	April 2012
Dissociative Photoionization of Quinoline and Isoquinoline Bouwman, Jordy; Sztáray, Bálint; Oomens, Jos The Journal of Physical Chemistry A, Vol. 119, Issue 7 https://doi.org/10.1021/jp5121993	journal	February 2015
Reaction of the C ₂ H Radical with 1-Butyne (C ₄ H ₆ ): Low-Temperature Kinetics and Isomer-Specific Product Detection ^† Soorkia, Satchin; Trevitt, Adam J.; Selby, Talitha M. The Journal of Physical Chemistry A, Vol. 114, Issue 9 https://doi.org/10.1021/jp911132r	journal	March 2010
Mechanism of Synthesis of Adenine from Hydrogen Cyanide under Possible Primitive Earth Conditions OrÓ, J. Nature, Vol. 191, Issue 4794 https://doi.org/10.1038/1911193a0	journal	September 1961
Infrared and reflectron time-of-flight mass spectroscopic study on the synthesis of glycolaldehyde in methanol (CH ₃ OH) and methanol–carbon monoxide (CH ₃ OH–CO) ices exposed to ionization radiation Maity, Surajit; Kaiser, Ralf I.; Jones, Brant M. Faraday Discussions, Vol. 168 https://doi.org/10.1039/C3FD00121K	journal	January 2014
Organic compounds in carbonaceous meteorites Sephton, Mark A. Natural Product Reports, Vol. 19, Issue 3 https://doi.org/10.1039/b103775g	journal	March 2002
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
A search for interstellar pyrimidine Kuan, Yi-Jehng; Yan, Chi-Hung; Charnley, Steven B. Monthly Notices of the Royal Astronomical Society, Vol. 345, Issue 2 https://doi.org/10.1046/j.1365-8711.2003.06975.x	journal	October 2003
Formation and photostability of N-heterocycles in space: I. The effect of nitrogen on the photostability of small aromatic molecules Peeters, Z.; Botta, O.; Charnley, S. B. Astronomy & Astrophysics, Vol. 433, Issue 2 https://doi.org/10.1051/0004-6361:20042443	journal	March 2005
Detection of circumstellar CH ₂ CHCN, CH ₂ CN, CH ₃ CCH, and H ₂ CS Agúndez, M.; Fonfría, J. P.; Cernicharo, J. Astronomy & Astrophysics, Vol. 479, Issue 2 https://doi.org/10.1051/0004-6361:20078956	journal	January 2008
The formation of Polycyclic Aromatic Hydrocarbons in evolved circumstellar environments Cherchneff, I. EAS Publications Series, Vol. 46 https://doi.org/10.1051/eas/1146019	journal	January 2011
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
Chemical evolution: The mechanism of the formation of adenine under prebiotic conditions Roy, D.; Najafian, K.; von Rague Schleyer, P. Proceedings of the National Academy of Sciences, Vol. 104, Issue 44 https://doi.org/10.1073/pnas.0708434104	journal	October 2007
Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases Callahan, M. P.; Smith, K. E.; Cleaves, H. J. Proceedings of the National Academy of Sciences, Vol. 108, Issue 34 https://doi.org/10.1073/pnas.1106493108	journal	August 2011
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
New circumstellar cyanoacetylene sources Jewell, P. R.; Snyder, L. E. The Astrophysical Journal, Vol. 255 https://doi.org/10.1086/183771	journal	April 1982
[ITAL]Infrared Space Observatory's[/ITAL] Discovery of C[TINF]4[/TINF]H[TINF]2[/TINF], C[TINF]6[/TINF]H[TINF]2[/TINF], and Benzene in CRL 618 Cernicharo, José; Heras, Ana M.; Tielens, A. G. G. M. The Astrophysical Journal, Vol. 546, Issue 2 https://doi.org/10.1086/318871	journal	January 2001
Variations in the Peak Position of the 6.2 μm Interstellar Emission Feature: A Tracer of N in the Interstellar Polycyclic Aromatic Hydrocarbon Population Hudgins, Douglas M.; Bauschlicher, Jr., Charles W.; Allamandola, L. J. The Astrophysical Journal, Vol. 632, Issue 1 https://doi.org/10.1086/432495	journal	October 2005
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
Infrared Spectra of Isolated Protonated Polycyclic Aromatic Hydrocarbon Molecules Knorke, Harald; Langer, Judith; Oomens, Jos The Astrophysical Journal, Vol. 706, Issue 1 https://doi.org/10.1088/0004-637X/706/1/L66	journal	October 2009
The Photochemistry of Pyrimidine in Realistic Astrophysical ices and the Production of Nucleobases Nuevo, Michel; Materese, Christopher K.; Sandford, Scott A. The Astrophysical Journal, Vol. 793, Issue 2 https://doi.org/10.1088/0004-637X/793/2/125	journal	September 2014
Champagne flutes and brandy snifters: modelling protostellar outflow–cloud chemical interfaces Rollins, R. P.; Rawlings, J. M. C.; Williams, D. A. Monthly Notices of the Royal Astronomical Society, Vol. 443, Issue 4 https://doi.org/10.1093/mnras/stu1347	journal	August 2014
UV Irradiation of Polycyclic Aromatic Hydrocarbons in Ices: Production of Alcohols, Quinones, and Ethers Bernstein, M. P. Science, Vol. 283, Issue 5405 https://doi.org/10.1126/science.283.5405.1135	journal	February 1999
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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Valence Photoionization of Thymine: Ionization Energies, Vibrational Structure, and Fragmentation Pathways from the Slow to the Ultrafast Majer, Katharina; Signorell, Ruth; Heringa, Maarten F. Chemistry – A European Journal, Vol. 25, Issue 62 https://doi.org/10.1002/chem.201903282	journal	October 2019
On the formation and the isomer specific detection of methylacetylene (CH ₃ CCH), propene (CH ₃ CHCH ₂ ), cyclopropane (c-C ₃ H ₆ ), vinylacetylene (CH ₂ CHCCH), and 1,3-butadiene (CH ₂ CHCHCH ₂ ) from interstellar methane ice analogues Abplanalp, Matthew J.; Góbi, Sándor; Kaiser, Ralf I. Physical Chemistry Chemical Physics, Vol. 21, Issue 10 https://doi.org/10.1039/c8cp03921f	journal	January 2019
Nitrogen matters: the difference between PANH and PAH formation Bouwman, Jordy; Bodi, Andras; Hemberger, Patrick Physical Chemistry Chemical Physics, Vol. 20, Issue 47 https://doi.org/10.1039/c8cp05830j	journal	January 2018
Isoquinoline gas-phase absorption spectrum in the vacuum ultraviolet between 3.7 and 10.7 eV. New valence and Rydberg electronic states Leach, Sydney; Jones, Nykola C.; Hoffmann, Søren V. RSC Advances, Vol. 9, Issue 9 https://doi.org/10.1039/c8ra09725a	journal	January 2019
Synthesis of functionalized nitrogen-containing polycyclic aromatic hydrocarbons and other prebiotic compounds in impacting glycine solutions Kroonblawd, Matthew P.; Lindsey, Rebecca K.; Goldman, Nir Chemical Science, Vol. 10, Issue 24 https://doi.org/10.1039/c9sc00155g	journal	January 2019
Variations in the 6.2 μm emission profile in starburst-dominated galaxies: a signature of polycyclic aromatic nitrogen heterocycles (PANHs)? Canelo, Carla M.; Friaça, Amâncio C. S.; Sales, Dinalva A. Monthly Notices of the Royal Astronomical Society, Vol. 475, Issue 3 https://doi.org/10.1093/mnras/stx3351	journal	January 2018
Valence Photoionization of Thymine: Ionization Energies, Vibrational Structure, and Fragmentation Pathways from the Slow to the Ultrafast Katharina, Majer,; Ruth, Signorell,; F., Heringa, Maarten ETH Zurich https://doi.org/10.3929/ethz-b-000372255	text	January 2019
Variations in the 6.2 $μ$m emission profile in starburst-dominated galaxies: a signature of polycyclic aromatic nitrogen heterocycles (PANHs)? Canelo, C. M.; Friaça, A. C. S.; Sales, D. A. arXiv https://doi.org/10.48550/arxiv.1708.07565	text	January 2017

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