A molecular beam and computational study on the barrierless gas phase formation of (iso)quinoline in low temperature extraterrestrial environments

Zhao, Long; Prendergast, Matthew; Kaiser, Ralf I.; Xu, Bo; Lu, Wenchao; Ahmed, Musahid; Hasan Howlader, A.; Wnuk, Stanislaw F.; Korotchenko, Alexander S.; Evseev, Mikhail M.; Bashkirov, Eugene K.; Azyazov, Valeriy N.; Mebel, Alexander M.

doi:10.1039/d1cp02169a

Title: A molecular beam and computational study on the barrierless gas phase formation of (iso)quinoline in low temperature extraterrestrial environments

Journal Article · 06 August 2021 · Physical Chemistry Chemical Physics. PCCP

DOI: https://doi.org/10.1039/d1cp02169a · OSTI ID:1830779

Zhao, Long ^[1]; Prendergast, Matthew ^[2];

^[2]; Xu, Bo ^[3];

^[3];

^[4];

^[4]; Korotchenko, Alexander S. ^[5]; Evseev, Mikhail M. ^[5]; Bashkirov, Eugene K. ^[5]; Azyazov, Valeriy N. ^[6];

^[4]

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)
Samara National Research University (Russian Federation)
Samara National Research University (Russian Federation); Russian Academy of Sciences (RAS), Moscow (Russian Federation). P.N. Lebedev Physical Institute

Despite remarkable progress toward the understanding of the formation pathways leading to polycyclic aromatic hydrocarbons (PAHs) in combustion systems and in deep space, the complex reaction pathways leading to nitrogen-substituted PAHs (NPAHs) at low temperatures of molecular clouds and hydrocarbon-rich, nitrogen-containing atmospheres of planets and their moons like Titan have remained largely obscure. Here, we demonstrate through laboratory experiments and computations that the simplest prototype of NPAHs – quinoline and isoquinoline (C₉H₇N) – can be synthesized via rapid and de-facto barrier-less reactions involving o-, m- and p-pyridinyl radicals (C₅H₄N˙) with vinylacetylene (C₄H₄) under low-temperature conditions.

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

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

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

OSTI ID:: 1830779

Journal Information:: Physical Chemistry Chemical Physics. PCCP, Journal Name: Physical Chemistry Chemical Physics. PCCP Journal Issue: 34 Vol. 23; ISSN 1463-9076

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (66)

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
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. Angewandte Chemie International Edition, Vol. 56, Issue 16 https://doi.org/10.1002/anie.201701259	journal	March 2017
Indene Formation under Single-Collision Conditions from the Reaction of Phenyl Radicals with Allene and Methylacetylene-A Crossed Molecular Beam and Ab Initio Study Parker, Dr Dorian S. N.; Zhang, Dr Fangtong; Kaiser, Dr Ralf I. Chemistry - An Asian Journal, Vol. 6, Issue 11 https://doi.org/10.1002/asia.201100535	journal	September 2011
Gas‐Phase Synthesis of Triphenylene (C ₁₈ H ₁₂ ) Zhao, Long; Xu, Bo; Ablikim, Utuq ChemPhysChem, Vol. 20, Issue 6 https://doi.org/10.1002/cphc.201801154	journal	February 2019
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
Effect of the damping function in dispersion corrected density functional theory Grimme, Stefan; Ehrlich, Stephan; Goerigk, Lars Journal of Computational Chemistry, Vol. 32, Issue 7 https://doi.org/10.1002/jcc.21759	journal	March 2011
Titan as Revealed by the Cassini Radar Lopes, R. M. C.; Wall, S. D.; Elachi, C. Space Science Reviews, Vol. 215, Issue 4 https://doi.org/10.1007/s11214-019-0598-6	journal	May 2019
Nitrogen Atmospheres of the Icy Bodies in the Solar System Scherf, M.; Lammer, H.; Erkaev, N. V. Space Science Reviews, Vol. 216, Issue 8 https://doi.org/10.1007/s11214-020-00752-0	journal	October 2020
Organic compounds in the Forest Vale, H4 ordinary chondrite Zenobi, Renato; Philippoz, Jean-Michel; Zare, Richard N. Geochimica et Cosmochimica Acta, Vol. 56, Issue 7 https://doi.org/10.1016/0016-7037(92)90366-Q	journal	July 1992
Basis set convergence in second-row compounds. The importance of core polarization functions Martin, Jan M. L.; Uzan, Olivier Chemical Physics Letters, Vol. 282, Issue 1 https://doi.org/10.1016/S0009-2614(97)01128-7	journal	January 1998
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
Isotopic evidence from an Antarctic carbonaceous chondrite for two reaction pathways of extraterrestrial PAH formation Naraoka, Hiroshi; Shimoyama, Akira; Harada, Kaoru Earth and Planetary Science Letters, Vol. 184, Issue 1 https://doi.org/10.1016/S0012-821X(00)00316-2	journal	December 2000
Investigating repetitive reaction pathways for the formation of polycyclic aromatic hydrocarbons in combustion processes Hansen, Nils; Schenk, Marina; Moshammer, Kai Combustion and Flame, Vol. 180 https://doi.org/10.1016/j.combustflame.2016.09.013	journal	June 2017
First aromatic ring formation by the radical-chain reaction of vinylacetylene and propargyl Jin, Hanfeng; Xing, Lili; Liu, Dapeng Combustion and Flame, Vol. 225 https://doi.org/10.1016/j.combustflame.2020.11.034	journal	March 2021
Extraterrestrial nucleobases in the Murchison meteorite Martins, Zita; Botta, Oliver; Fogel, Marilyn L. Earth and Planetary Science Letters, Vol. 270, Issue 1-2 https://doi.org/10.1016/j.epsl.2008.03.026	journal	June 2008
Rapid soot inception via α-alkynyl substitution of polycyclic aromatic hydrocarbons Liu, Peng; Jin, Hanfeng; Chen, Bingjie Fuel, Vol. 295 https://doi.org/10.1016/j.fuel.2021.120580	journal	July 2021
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
Investigation of pyridine carboxylic acids in CM2 carbonaceous chondrites: Potential precursor molecules for ancient coenzymes Smith, Karen E.; Callahan, Michael P.; Gerakines, Perry A. Geochimica et Cosmochimica Acta, Vol. 136 https://doi.org/10.1016/j.gca.2014.04.001	journal	July 2014
Combustion chemistry probed by synchrotron VUV photoionization mass spectrometry Qi, Fei Proceedings of the Combustion Institute, Vol. 34, Issue 1 https://doi.org/10.1016/j.proci.2012.09.002	journal	January 2013
Gas-Phase Formation of C ₅ H ₆ Isomers via the Crossed Molecular Beam Reaction of the Methylidyne Radical (CH; X ² Π) with 1,2-Butadiene (CH ₃ CHCCH ₂ ; X ¹ A′) He, Chao; Nikolayev, Anatoliy A.; Zhao, Long The Journal of Physical Chemistry A, Vol. 125, Issue 1 https://doi.org/10.1021/acs.jpca.0c08731	journal	January 2021
An Aromatic Universe–A Physical Chemistry Perspective Kaiser, Ralf I.; Hansen, Nils The Journal of Physical Chemistry A, Vol. 125, Issue 18 https://doi.org/10.1021/acs.jpca.1c00606	journal	April 2021
Formation Mechanisms of Naphthalene and Indene: From the Interstellar Medium to Combustion Flames Mebel, Alexander M.; Landera, Alexander; Kaiser, Ralf I. The Journal of Physical Chemistry A, Vol. 121, Issue 5 https://doi.org/10.1021/acs.jpca.6b09735	journal	January 2017
Combined Experimental and Computational Investigation of the Elementary Reaction of Ground State Atomic Carbon (C; ³ P _j ) with Pyridine (C ₅ H ₅ N; X ¹ A ₁ ) via Ring Expansion and Ring Degradation Pathways Lucas, Michael; Thomas, Aaron M.; Kaiser, Ralf I. The Journal of Physical Chemistry A, Vol. 122, Issue 12 https://doi.org/10.1021/acs.jpca.8b00756	journal	March 2018
Functional Relationships between Kinetic, Flow, and Geometrical Parameters in a High-Temperature Chemical Microreactor Zagidullin, M. V.; Kaiser, R. I.; Porfiriev, D. P. The Journal of Physical Chemistry A, Vol. 122, Issue 45 https://doi.org/10.1021/acs.jpca.8b06837	journal	October 2018
Time- and Isomer-Resolved Measurements of Sequential Addition of Acetylene to the Propargyl Radical Savee, John D.; Selby, Talitha M.; Welz, Oliver The Journal of Physical Chemistry Letters, Vol. 6, Issue 20 https://doi.org/10.1021/acs.jpclett.5b01896	journal	September 2015
VUV Photoionization Study of the Formation of the Simplest Polycyclic Aromatic Hydrocarbon: Naphthalene (C ₁₀ H ₈ ) Zhao, Long; Kaiser, Ralf I.; Xu, Bo The Journal of Physical Chemistry Letters, Vol. 9, Issue 10 https://doi.org/10.1021/acs.jpclett.8b01020	journal	May 2018
Efficient and Accurate Double-Hybrid-Meta-GGA Density Functionals—Evaluation with the Extended GMTKN30 Database for General Main Group Thermochemistry, Kinetics, and Noncovalent Interactions Goerigk, Lars; Grimme, Stefan Journal of Chemical Theory and Computation, Vol. 7, Issue 2 https://doi.org/10.1021/ct100466k	journal	December 2010
Potential Purine Antagonists. XV. Preparation of Some 6,8-Disubstituted Purines ¹ Robins, Roland K. Journal of the American Chemical Society, Vol. 80, Issue 24 https://doi.org/10.1021/ja01557a051	journal	December 1958
Theoretical Study on Reaction Mechanism of Ground-State Cyano Radical with 1,3-Butadiene: Prospect of Pyridine Formation Sun, B. J.; Huang, C. H.; Chen, S. Y. The Journal of Physical Chemistry A, Vol. 118, Issue 36 https://doi.org/10.1021/jp5056864	journal	August 2014
Gas phase synthesis of [4]-helicene Zhao, Long; Kaiser, Ralf I.; Xu, Bo Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-09224-8	journal	April 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
Pyrene synthesis in circumstellar envelopes and its role in the formation of 2D nanostructures Zhao, Long; Kaiser, Ralf I.; Xu, Bo Nature Astronomy, Vol. 2, Issue 5 https://doi.org/10.1038/s41550-018-0399-y	journal	March 2018
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
Chemical dynamics of the CH(X ² Π) + C ₂ H ₄ (X ¹ A _1g ), CH(X ² Π) + C ₂ D ₄ (X ¹ A _1g ), and CD(X ² Π) + C ₂ H ₄ (X ¹ A _1g ) reactions studied under single collision conditions Zhang, Fangtong; Maksyutenko, Pavlo; Kaiser, Ralf I. Phys. Chem. Chem. Phys., Vol. 14, Issue 2 https://doi.org/10.1039/C1CP22350J	journal	January 2012
On the formation of pyridine in the interstellar medium Parker, Dorian S. N.; Kaiser, Ralf I.; Kostko, Oleg Physical Chemistry Chemical Physics, Vol. 17, Issue 47 https://doi.org/10.1039/C5CP02960K	journal	January 2015
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
How to add a five-membered ring to polycyclic aromatic hydrocarbons (PAHs) – molecular mass growth of the 2-naphthyl radical (C 10 H 7 ) to benzindenes (C 13 H 10 ) as a case study Zhao, Long; Prendergast, Matthew; Kaiser, Ralf I. Physical Chemistry Chemical Physics, Vol. 21, Issue 30 https://doi.org/10.1039/C9CP02930C	journal	January 2019
Role of ring-enlargement reactions in the formation of aromatic hydrocarbons Baroncelli, Martina; Mao, Qian; Galle, Simon Physical Chemistry Chemical Physics, Vol. 22, Issue 8 https://doi.org/10.1039/C9CP05854K	journal	January 2020
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
Gas-phase synthesis of corannulene – a molecular building block of fullerenes Zhao, Long; Doddipatla, Srinivas; Kaiser, Ralf I. Physical Chemistry Chemical Physics, Vol. 23, Issue 10 https://doi.org/10.1039/D0CP06537D	journal	January 2021
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
Direct detection of pyridine formation by the reaction of CH (CD) with pyrrole: a ring expansion reaction Soorkia, Satchin; Taatjes, Craig A.; Osborn, David L. Physical Chemistry Chemical Physics, Vol. 12, Issue 31 https://doi.org/10.1039/c002135k	journal	January 2010
Photodissociation of benzene under collision-free conditions: An ab initio /Rice–Ramsperger–Kassel–Marcus study Kislov, V. V.; Nguyen, T. L.; Mebel, A. M. The Journal of Chemical Physics, Vol. 120, Issue 15 https://doi.org/10.1063/1.1676275	journal	April 2004
Photodynamics of Molecules in Space McCarroll, Ronald THE PHYSICS OF IONIZED GASES: 22nd Summer School and International Symposium on the Physics of Ionized Gases; Invited Lectures, Topical Invited Lectures and Progress Reports, AIP Conference Proceedings https://doi.org/10.1063/1.1843491	conference	January 2004
Photodissociation dynamics of pyridine Lin, Ming-Fu; Dyakov, Yuri A.; Tseng, Chien-Ming The Journal of Chemical Physics, Vol. 123, Issue 5 https://doi.org/10.1063/1.1994849	journal	August 2005
Semiempirical hybrid density functional with perturbative second-order correlation Grimme, Stefan The Journal of Chemical Physics, Vol. 124, Issue 3 https://doi.org/10.1063/1.2148954	journal	January 2006
A simple and efficient CCSD(T)-F12 approximation Adler, Thomas B.; Knizia, Gerald; Werner, Hans-Joachim The Journal of Chemical Physics, Vol. 127, Issue 22 https://doi.org/10.1063/1.2817618	journal	December 2007
Simplified CCSD(T)-F12 methods: Theory and benchmarks Knizia, Gerald; Adler, Thomas B.; Werner, Hans-Joachim The Journal of Chemical Physics, Vol. 130, Issue 5 https://doi.org/10.1063/1.3054300	journal	February 2009
Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen Dunning, Thom H. The Journal of Chemical Physics, Vol. 90, Issue 2 https://doi.org/10.1063/1.456153	journal	January 1989
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Gaussian-3 (G3) theory for molecules containing first and second-row atoms Curtiss, Larry A.; Raghavachari, Krishnan; Redfern, Paul C. The Journal of Chemical Physics, Vol. 109, Issue 18 https://doi.org/10.1063/1.477422	journal	November 1998
Gaussian-3 theory using density functional geometries and zero-point energies Baboul, Anwar G.; Curtiss, Larry A.; Redfern, Paul C. The Journal of Chemical Physics, Vol. 110, Issue 16 https://doi.org/10.1063/1.478676	journal	April 1999
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
Chemical Evolution of Carbonaceous Material in Interstellar Clouds Duley, W. W. The Astrophysical Journal, Vol. 528, Issue 2 https://doi.org/10.1086/308204	journal	January 2000
The Astrobiology of Nucleobases Peeters, Z.; Botta, O.; Charnley, S. B. The Astrophysical Journal, Vol. 593, Issue 2 https://doi.org/10.1086/378346	journal	July 2003
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
A CROSSED MOLECULAR BEAM, LOW-TEMPERATURE KINETICS, AND THEORETICAL INVESTIGATION OF THE REACTION OF THE CYANO RADICAL (CN) WITH 1,3-BUTADIENE (C ₄ H ₆ ). A ROUTE TO COMPLEX NITROGEN-BEARING MOLECULES IN LOW-TEMPERATURE EXTRATERRESTRIAL ENVIRONMENTS Morales, Sébastien B.; Bennett, Christopher J.; Le Picard, Sébastien D. The Astrophysical Journal, Vol. 742, Issue 1 https://doi.org/10.1088/0004-637X/742/1/26	journal	November 2011
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
Resonance-stabilized hydrocarbon-radical chain reactions may explain soot inception and growth Johansson, K. O.; Head-Gordon, M. P.; Schrader, P. E. Science, Vol. 361, Issue 6406 https://doi.org/10.1126/science.aat3417	journal	September 2018
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
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
Molecular and Isotopic Distributions of PAHs from Three Antarctic Carbonaceous Chondrites (CM2) Naraoka, H. Mineralogical Magazine, Vol. 62A, Issue 2 https://doi.org/10.1180/minmag.1998.62A.2.219	journal	January 1998
Discovery of Interstellar trans -cyanovinylacetylene (HC ≡ CCH = CHC ≡ N) and vinylcyanoacetylene (H ₂ C = CHC ₃ N) in GOTHAM Observations of TMC-1 Kelvin Lee, Kin Long; Loomis, Ryan A.; Burkhardt, Andrew M. The Astrophysical Journal, Vol. 908, Issue 1 https://doi.org/10.3847/2041-8213/abdbb9	journal	February 2021