Low-Temperature Gas-Phase Formation of Methanimine (CH2NH; X1A')–the Simplest Imine–under Single-Collision Conditions

Yang, Zhenghai; Medvedkov, Iakov A.; Goettl, Shane J.; Kaiser, Ralf I.

doi:10.1021/acs.jpclett.3c02360

Title: Low-Temperature Gas-Phase Formation of Methanimine (CH₂NH; X¹A')–the Simplest Imine–under Single-Collision Conditions

Journal Article · 17 September 2023 · Journal of Physical Chemistry Letters

DOI: https://doi.org/10.1021/acs.jpclett.3c02360 · OSTI ID:2278904

Yang, Zhenghai ^[1]; Medvedkov, Iakov A. ^[2];

^[2];

^[2]

University of Hawaii at Manoa, Honolulu, HI (United States); University of Hawaii
University of Hawaii at Manoa, Honolulu, HI (United States)

The D1-methanimine molecule (CHDNH; X¹A') – the simplest (deuterated) imine – has been prepared through the elementary reaction of the D1-methylidyne (CD; X²Π) with ammonia (NH₃; X¹A₁) under single collision conditions. As a highly reactive species with a carbon-nitrogen double bond and a key building block of biomolecules like amino acids and nucleobases, methanimine is of particular significance in coupling the nitrogen and carbon chemistries in the interstellar medium and in hydrocarbon-rich atmospheres of planets and their moons. However, the underlying formation mechanisms of methanimine in these extreme environments are still elusive. Here, the directed, low-temperature gas-phase formation of D1-methanimine will deepen our fundamental understanding of low-temperature molecular growths processes via carbon-nitrogen bond coupling. Considering the recent detection of the interstellar D1-methylidyne radical, the investigation of the CD–NH₃ system also suggests a promising pathway for future astronomical observations of D1-methanimine as a molecular tracer of gas phase deuterium-enrichment in deep space.

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

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

Grant/Contract Number:: FG02-03ER15411

OSTI ID:: 2278904

Journal Information:: Journal of Physical Chemistry Letters, Journal Name: Journal of Physical Chemistry Letters Journal Issue: 38 Vol. 14; ISSN 1948-7185

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (46)

Gas-Phase Preparation of 1-Germavinylidene (H₂CGe; X¹A₁), the Isovalent Counterpart of Vinylidene (H₂CC; X¹A₁), via Non-adiabatic Dynamics through the Elementary Reaction of Ground State Atomic Carbon (C; ³P) with Germane (GeH₄; X¹A₁) Yang, Zhenghai; Sun, Bing-Jian; He, Chao The Journal of Physical Chemistry Letters, Vol. 14, Issue 2 https://doi.org/10.1021/acs.jpclett.2c03749	journal	January 2023
Nature'S Starships. i. Observed Abundances and Relative Frequencies of Amino Acids in Meteorites Cobb, Alyssa K.; Pudritz, Ralph E. The Astrophysical Journal, Vol. 783, Issue 2 https://doi.org/10.1088/0004-637X/783/2/140	journal	February 2014
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
First detection of deuterated methylidyne (CD) in the interstellar medium Jacob, Arshia M.; Menten, Karl M.; Wyrowski, Friedrich Astronomy & Astrophysics, Vol. 675 https://doi.org/10.1051/0004-6361/202245209	journal	July 2023
Ultralow-Temperature Kinetics of CH(X ² Π) Reactions: Rate Coefficients for Reactions with O ₂ and NO ( T = 13−708 K), and with NH ₃ ( T = 23−295 K) Bocherel, Pascal; Herbert, Lee B.; Rowe, Bertrand R. The Journal of Physical Chemistry, Vol. 100, Issue 8 https://doi.org/10.1021/jp952628f	journal	January 1996
Methanimine as a Key Precursor of Imines in the Interstellar Medium: The Case of Propargylimine Lupi, Jacopo; Puzzarini, Cristina; Barone, Vincenzo The Astrophysical Journal Letters, Vol. 903, Issue 2 https://doi.org/10.3847/2041-8213/abc25c	journal	November 2020
Prebiotic chemicals—amino acid and phosphorus—in the coma of comet 67P/Churyumov-Gerasimenko Altwegg, Kathrin; Balsiger, Hans; Bar-Nun, Akiva Science Advances, Vol. 2, Issue 5 https://doi.org/10.1126/sciadv.1600285	journal	May 2016
Microwave detection of the molecular transient methyleneimine (CH2=NH) Johnson, Donald R.; Lovas, Frank J. Chemical Physics Letters, Vol. 15, Issue 1 https://doi.org/10.1016/0009-2614(72)87017-9	journal	July 1972
Elementary reactions of N atoms with hydrocarbons: first steps towards the formation of prebiotic N-containing molecules in planetary atmospheres Balucani, Nadia Chemical Society Reviews, Vol. 41, Issue 16 https://doi.org/10.1039/c2cs35113g	journal	January 2012
Ultraviolet Survey of CO and H ₂ in Diffuse Molecular Clouds: The Reflection of Two Photochemistry Regimes in Abundance Relationships Sheffer, Y.; Rogers, M.; Federman, S. R. The Astrophysical Journal, Vol. 687, Issue 2 https://doi.org/10.1086/591484	journal	November 2008
Laboratory spectroscopy of allylimine and tentative detection towards the G+0.693-0.027 molecular cloud Alberton, D.; Bizzocchi, L.; Jiang, N. Astronomy & Astrophysics, Vol. 669 https://doi.org/10.1051/0004-6361/202244618	journal	January 2023
Kinetics of methylidyne (CH X 2Π) radical reactions with ammonia and methylamines Zabarnick, S.; Fleming, J. W.; Lin, M. C. Chemical Physics, Vol. 132, Issue 3 https://doi.org/10.1016/0301-0104(89)80034-5	journal	April 1989
A Rigorous Attempt to Verify Interstellar Glycine Snyder, L. E.; Lovas, F. J.; Hollis, J. M. The Astrophysical Journal, Vol. 619, Issue 2 https://doi.org/10.1086/426677	journal	February 2005
Detection of E-Cyanomethanimine Toward Sagittarius B2(N) in the Green bank Telescope Primos Survey Zaleski, Daniel P.; Seifert, Nathan A.; Steber, Amanda L. The Astrophysical Journal, Vol. 765, Issue 1 https://doi.org/10.1088/2041-8205/765/1/L10	journal	February 2013
Predictions of gas-phase methanimine (CH2NH) abundance in cold cores Luthra, H.; Wakelam, V.; Sharma, M. K. Monthly Notices of the Royal Astronomical Society, Vol. 521, Issue 2 https://doi.org/10.1093/mnras/stad668	journal	March 2023
Directed Gas-Phase Formation of Aminosilylene (HSiNH₂; X¹A′): The Simplest Silicon Analogue of an Aminocarbene, under Single-Collision Conditions Yang, Zhenghai; He, Chao; Goettl, Shane Journal of the American Chemical Society, Vol. 143, Issue 35 https://doi.org/10.1021/jacs.1c05510	journal	August 2021
Gas-phase reactions. 66. Gas-phase pyrolyses of alkyl azides: experimental evidence for chemical activation Bock, Hans.; Dammel, Ralph. Journal of the American Chemical Society, Vol. 110, Issue 16 https://doi.org/10.1021/ja00224a004	journal	August 1988
Propargylimine in the laboratory and in space: millimetre-wave spectroscopy and its first detection in the ISM Bizzocchi, L.; Prudenzano, D.; Rivilla, V. M. Astronomy & Astrophysics, Vol. 640 https://doi.org/10.1051/0004-6361/202038083	journal	August 2020
Detection of HNCCC in TMC-1 Kawaguchi, Kentarou; Takano, Shuro; Ohishi, Masatoshi The Astrophysical Journal, Vol. 396 https://doi.org/10.1086/186514	journal	September 1992
Cyanomethanimine Isomers in cold Interstellar Clouds: Insights from Electronic Structure and Kinetic Calculations Vazart, Fanny; Latouche, Camille; Skouteris, Dimitrios The Astrophysical Journal, Vol. 810, Issue 2 https://doi.org/10.1088/0004-637X/810/2/111	journal	September 2015
Combined Crossed Molecular Beam and Theoretical Studies of the N( ² D) + CH ₄ Reaction and Implications for Atmospheric Models of Titan ^† Balucani, Nadia; Bergeat, Astrid; Cartechini, Laura The Journal of Physical Chemistry A, Vol. 113, Issue 42 https://doi.org/10.1021/jp904302g	journal	October 2009
Rate Constants and Branching Ratios for the Reaction of CH Radicals with NH ₃ : A Combined Experimental and Theoretical Study Blitz, Mark A.; Talbi, Dahbia; Seakins, Paul W. The Journal of Physical Chemistry A, Vol. 116, Issue 24 https://doi.org/10.1021/jp209383t	journal	December 2011
Ion chemistry and N-containing molecules in Titan's upper atmosphere Vuitton, V.; Yelle, R. V.; McEwan, M. J. Icarus, Vol. 191, Issue 2 https://doi.org/10.1016/j.icarus.2007.06.023	journal	November 2007
Dimerization of methanimine and its charged species in the atmosphere of Titan and interstellar/cometary ice analogs Skouteris, Dimitrios; Balucani, Nadia; Faginas-Lago, Noelia Astronomy & Astrophysics, Vol. 584 https://doi.org/10.1051/0004-6361/201526978	journal	November 2015
NH3 in Orion-KL - A new interpretation Genzel, R.; Ho, P. T. P.; Bieging, J. The Astrophysical Journal, Vol. 259 https://doi.org/10.1086/183856	journal	August 1982
The Physics and Chemistry of Small Translucent Molecular Clouds. XII. More Complex Species Explainable by Gas‐Phase Processes Turner, B. E.; Terzieva, R.; Herbst, Eric The Astrophysical Journal, Vol. 518, Issue 2 https://doi.org/10.1086/307300	journal	June 1999
Interstellar Ammonia Ho, Paul T. P.; Townes, Charles H. Annual Review of Astronomy and Astrophysics, Vol. 21, Issue 1 https://doi.org/10.1146/annurev.aa.21.090183.001323	journal	September 1983
The role of isovalency in the reactions of the cyano (CN), boron monoxide (BO), silicon nitride (SiN), and ethynyl (C ₂ H) radicals with unsaturated hydrocarbons acetylene (C ₂ H ₂ ) and ethylene (C ₂ H ₄ ) Parker, D. S. N.; Mebel, A. M.; Kaiser, R. I. Chem. Soc. Rev., Vol. 43, Issue 8 https://doi.org/10.1039/C3CS60328H	journal	January 2014
Detection of Ketenimine (CH ₂ CNH) in Sagittarius B2(N) Hot Cores Lovas, F. J.; Hollis, J. M.; Remijan, Anthony J. The Astrophysical Journal, Vol. 645, Issue 2 https://doi.org/10.1086/506324	journal	June 2006
Identification of the interstellar cyanomethyl radical (CH2CN) in the molecular clouds TMC-1 and Sagittarius B2 Irvine, W. M.; Friberg, P.; Hjalmarson, A. The Astrophysical Journal, Vol. 334 https://doi.org/10.1086/185323	journal	November 1988
Formation of nitriles and imines in the atmosphere of Titan: combined crossed-beam and theoretical studies on the reaction dynamics of excited nitrogen atoms N(2D) with ethane Balucani, Nadia; Leonori, Francesca; Petrucci, Raffaele Faraday Discussions, Vol. 147 https://doi.org/10.1039/c004748a	journal	January 2010
THE DETECTION OF INTERSTELLAR ETHANIMINE (CH ₃ CHNH) FROM OBSERVATIONS TAKEN DURING THE GBT PRIMOS SURVEY Loomis, Ryan A.; Zaleski, Daniel P.; Steber, Amanda L. The Astrophysical Journal, Vol. 765, Issue 1 https://doi.org/10.1088/2041-8205/765/1/L9	journal	February 2013
Detection of two interstellar polycyclic aromatic hydrocarbons via spectral matched filtering McGuire, Brett A.; Loomis, Ryan A.; Burkhardt, Andrew M. Science, Vol. 371, Issue 6535 https://doi.org/10.1126/science.abb7535	journal	March 2021
Reaction dynamics of carbon-bearing radicals in circumstellar envelopes of carbon stars Gu, Xibin; Guo, Ying; Zhang, Fangtong Faraday Discussions, Vol. 133 https://doi.org/10.1039/b516457e	journal	January 2006
Molecular-beam scattering Vernon, M. F. https://doi.org/10.2172/5885401	report	July 1983
Abundant Z-cyanomethanimine in the interstellar medium: paving the way to the synthesis of adenine Rivilla, V. M.; Martín-Pintado, J.; Jiménez-Serra, I. Monthly Notices of the Royal Astronomical Society: Letters, Vol. 483, Issue 1 https://doi.org/10.1093/mnrasl/sly228	journal	December 2018
Molecular Reaction Dynamics Levine, Raphael D. https://doi.org/10.1017/CBO9780511614125	book	January 2005
SURVEY OBSERVATIONS OF A POSSIBLE GLYCINE PRECURSOR, METHANIMINE (CH₂NH) Suzuki, Taiki; Ohishi, Masatoshi; Hirota, Tomoya The Astrophysical Journal, Vol. 825, Issue 1 https://doi.org/10.3847/0004-637X/825/1/79	journal	July 2016
A Crossed Molecular Beam Study on the Reaction of Boron Atoms with Methylacetylene and Partially Deuterated Methylacetylene Zhang, Fangtong; Kao, Chih Hao; Chang, Agnes H. H. ChemPhysChem, Vol. 9, Issue 1 https://doi.org/10.1002/cphc.200700502	journal	January 2008
A Production of Amino Acids Under Possible Primitive Earth Conditions Miller, S. L. Science, Vol. 117, Issue 3046 https://doi.org/10.1126/science.117.3046.528	journal	May 1953
Microwave spectrum and molecular structure of methylenimine (CH2NH) Pearson, Richard; Lovas, Frank J. The Journal of Chemical Physics, Vol. 66, Issue 9 https://doi.org/10.1063/1.434490	journal	May 1977
Experimental investigation of aminoacetonitrile formation through the Strecker synthesis in astrophysical-like conditions: reactivity of methanimine (CH₂NH), ammonia (NH₃), and hydrogen cyanide (HCN) Danger, G.; Borget, F.; Chomat, M. Astronomy & Astrophysics, Vol. 535 https://doi.org/10.1051/0004-6361/201117602	journal	November 2011
Product Detection of the CH Radical Reactions with Ammonia and Methyl-Substituted Amines Bourgalais, Jeremy; Caster, Kacee L.; Durif, Olivier The Journal of Physical Chemistry A, Vol. 123, Issue 11 https://doi.org/10.1021/acs.jpca.8b11688	journal	February 2019
Chemical dynamics study on the gas-phase reaction of the D1-silylidyne radical (SiD; X ² Π) with deuterium sulfide (D ₂ S) and hydrogen sulfide (H ₂ S) Goettl, Shane J.; Doddipatla, Srinivas; Yang, Zhenghai Physical Chemistry Chemical Physics, Vol. 23, Issue 24 https://doi.org/10.1039/D1CP01629F	journal	January 2021
Green Bank Telescope Detection of New Interstellar Aldehydes: Propenal and Propanal Hollis, J. M.; Jewell, P. R.; Lovas, F. J. The Astrophysical Journal, Vol. 610, Issue 1 https://doi.org/10.1086/423200	journal	June 2004
ALMA Detection of Interstellar Methoxymethanol (CH ₃ OCH ₂ OH) McGuire, Brett A.; Shingledecker, Christopher N.; Willis, Eric R. The Astrophysical Journal, Vol. 851, Issue 2 https://doi.org/10.3847/2041-8213/aaa0c3	journal	December 2017

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Title: Low-Temperature Gas-Phase Formation of Methanimine (CH2NH; X1A')–the Simplest Imine–under Single-Collision Conditions

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Title: Low-Temperature Gas-Phase Formation of Methanimine (CH₂NH; X¹A')–the Simplest Imine–under Single-Collision Conditions