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Low-temperature formation of pyridine and (iso)quinoline via neutral–neutral reactions

Nature Astronomy (2024)Cite this article

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Abstract

Aromatic molecules represent fundamental building blocks in prebiotic chemistry and are contemplated as vital precursors to DNA and RNA nitrogen bases. However, despite the identification of some 300 molecules in extraterrestrial environments, the pathways to pyridine (C5H5N), pyridinyl (C5H4N·) and (iso)quinoline (C9H7N)—the simplest representative mono- and bicyclic aromatic molecules carrying nitrogen—are elusive. Here we afford compelling evidence on the gas-phase formation of methylene amidogen (H2CN·) and cyanomethyl (H2CCN·) radicals via molecular beam studies and electronic structure calculations. The modelling of the chemistries of the Taurus molecular cloud (TMC-1) and Titan’s atmosphere contemplates a complex chain of reactions synthesizing pyridine, pyridinyl and (iso)quinoline from H2CN· and H2CCN· at levels of up to 75%. This study affords unique entry points to precursors of DNA and RNA nitrogen bases in hydrocarbon-rich extraterrestrial environments thus changing the way we think about the origin of prebiotic molecules in our Galaxy.

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Fig. 1: Pathways to pyridine and (iso)quinoline.
Fig. 2: Laboratory data of the C–ND3 and C2–NH3 reactions.
Fig. 3: CM functions of the C–ND3 and C2–NH3 reactions.
Fig. 4: PESs of the reactions of C–ND3.
Fig. 5: Results of the astrochemical model for Titan’s atmosphere.
Fig. 6: Results of the astrochemical model for TMC-1.

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Data availability

All data generated in this study are available in the main text and Supplementary Information.

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Acknowledgements

This work was supported by the US Department of Energy, Basic Energy Sciences, by grant no. DE-FG02-03ER15411 to the University of Hawaii at Manoa. The support of Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), grant nos. 311508/2021-9 and 405524/2021-8, is also acknowledged. We acknowledge fruitful discussions on the fractional abundances of ammonia with C. A. Nixon (NASA Goddard) and K. Willacy (JPL).

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Authors and Affiliations

  1. Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI, USA

    Zhenghai Yang, Chao He, Shane J. Goettl & Ralf I. Kaiser

  2. Department of Chemistry and Biochemistry, Florida International University, Miami, FL, USA

    Alexander M. Mebel

  3. Centro Federal de Educação Tecnológica de Minas Gerais, CEFET-MG, Belo Horizonte, Brazil

    Paulo F. G. Velloso, Márcio O. Alves & Breno R. L. Galvão

  4. Institut des Sciences Moléculaires, CNRS, Université de Bordeaux, Talence, France

    Jean-Christophe Loison & Kevin M. Hickson

  5. Laboratoire d’Astrophysique de Bordeaux, Université de Bordeaux, CNRS, Pessac, France

    Michel Dobrijevic

  6. Xinjiang Astronomical Observatory, Chinese Academy of Sciences, Urumqi, P. R. China

    Xiaohu Li

  7. Key Laboratory of Radio Astronomy, Chinese Academy of Sciences, Urumqi, P. R. China

    Xiaohu Li

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Contributions

R.I.K. designed the experiments. Z.Y., C.H. and S.J.G. preformed the experiments. A.M.M., P.F.G.V., M.O.A. and B.R.L.G. conducted the electronic structure calculations. J.-C.L, K.M.H. and M.D. conducted the atmospheric modelling of Titan. X.L. performed the astrochemical modelling of TMC-1. Z.Y. and R.I.K. analysed the data and wrote the paper. All authors discussed the data.

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Correspondence to Alexander M. Mebel, Breno R. L. Galvão, Jean-Christophe Loison, Xiaohu Li or Ralf I. Kaiser.

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Extended data

Extended Data Fig. 1 Temperature and energy dependence of the thermal rate constants.

Temperature and energy dependence of the thermal rate constant k(T) and k(E) for the p3 + H in the C + NH3 reaction. TST methods are utilized in the calculation.

Extended Data Fig. 2 Potential energy surfaces of the reaction of dicarbon -ammonia.

Singlet and triplet surfaces of the C2-NH3 system involving different routes to the final products.

Extended Data Fig. 3 Formation pathways to pyridinyl radicals and the pyridine intermediate I.

Distinct pyridinyl radicals and pyridine can be formed from reactions of methylene amidogen (H2CN) with i/n-C4H3 isomers and the cyanomethyl (H2CCN) with propargyl (C3H3).

Extended Data Fig. 4 Formation pathways to pyridinyl radicals and the pyridine intermediate II.

Distinct pyridinyl radicals and pyridine can be formed from reactions of cis-iminomethyl (HCNH) with i/n-C4H3 isomers.

Supplementary information

Supplementary Information

Supplementary Notes 1–4, Figs. 1–3 and Tables 1–4.

Supplementary Data 1

Optimized Cartesian coordinates (Å) and vibrational frequencies (cm−1) for the intermediates, transition states, reactants and products involved in the reactions of C–NH3 and C2–NH3, and the pathways from H2CN·, cis-HCNH and H2CCN· to pyridine and pyridinyl radicals.

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Yang, Z., He, C., Goettl, S.J. et al. Low-temperature formation of pyridine and (iso)quinoline via neutral–neutral reactions. Nat Astron (2024). https://doi.org/10.1038/s41550-024-02267-y

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