n-Alkanes formed by methyl-methylene addition as a source of meteoritic aliphatics.
Journal
Communications chemistry
ISSN: 2399-3669
Titre abrégé: Commun Chem
Pays: England
ID NLM: 101725670
Informations de publication
Date de publication:
30 Jul 2024
30 Jul 2024
Historique:
received:
19
12
2023
accepted:
18
07
2024
medline:
31
7
2024
pubmed:
31
7
2024
entrez:
30
7
2024
Statut:
epublish
Résumé
Aliphatics prevail in asteroids, comets, meteorites and other bodies in our solar system. They are also found in the interstellar and circumstellar media both in gas-phase and in dust grains. Among aliphatics, linear alkanes (n-C
Identifiants
pubmed: 39080475
doi: 10.1038/s42004-024-01248-6
pii: 10.1038/s42004-024-01248-6
doi:
Types de publication
Journal Article
Langues
eng
Pagination
165Subventions
Organisme : Ministry of Economy and Competitiveness | Agencia Estatal de Investigación (Spanish Agencia Estatal de Investigación)
ID : PID2021-125309OA-I00
Organisme : Ministry of Economy and Competitiveness | Agencia Estatal de Investigación (Spanish Agencia Estatal de Investigación)
ID : TED2021-129416A-I00
Organisme : Ministry of Economy and Competitiveness | Agencia Estatal de Investigación (Spanish Agencia Estatal de Investigación)
ID : CNS2022-135658
Informations de copyright
© 2024. The Author(s).
Références
Alexander, C. M. O., Fogel, M., Yabuta, H. & Cody, G. D. The origin and evolution of chondrites recorded in the elemental and isotopic compositions of their macromolecular organic matter. Geochim. Cosmochim. Acta 71, 4380–4403 (2007).
doi: 10.1016/j.gca.2007.06.052
Sabbah, H. et al. Detection of cosmic fullerenes in the Almahata Sitta Meteorite: are they an interstellar heritage? Astrophys. J. 931, 91 (2022).
doi: 10.3847/1538-4357/ac69dd
Sandra, P. et al. The organic content of the Tagish lake meteorite. Science 293, 2236–2239 (2001).
doi: 10.1126/science.1062614
Botta, O. & Bada, J. L. Extraterrestrial organic compounds in meteorites. Surv. Geophys. 23, 411–467 (2002).
doi: 10.1023/A:1020139302770
Glavin, D. P. et al. in Primitive Meteorites and Asteroids Physical, Chemical and Spectroscopic Observations Paving the Way to Exploration (ed. Abreu, N.) 205–271 (Elsevier, 2018).
Nooner, D. W. & Oró, J. Organic compounds in meteorites—I. Aliphatic hydrocarbons. Geochim. Cosmochim. Acta 31, 1359–1394 (1967).
doi: 10.1016/0016-7037(67)90018-X
Martins, Z., Modica, P., Zanda, B. & d’Hendecourt, L. L. S. The amino acid and hydrocarbon contents of the Paris meteorite: insights into the most primitive CM chondrite. Meteorit. Planet. Sci. 50, 926–943 (2015).
doi: 10.1111/maps.12442
Mumma, M. J. et al. Detection of abundant ethane and methane, along with carbon monoxide and water, in Comet C/1996 B2 hyakutake: evidence for interstellar origin. Science 272, 1310–1314 (1996).
pubmed: 8650540
doi: 10.1126/science.272.5266.1310
Sephton, M. A., Pillinger, C. T. & Gilmour, I. Normal alkanes in meteorites: molecular δ13C values indicate an origin by terrestrial contamination. Precambrian Res. 106, 47–58 (2001).
doi: 10.1016/S0301-9268(00)00124-8
Joblin, C., Szczerba, R., Berné, O. & Szyszka, C. Carriers of the mid-IR emission bands in PNe reanalysed. Astron. Astrophys. 490, 189–196 (2008).
doi: 10.1051/0004-6361:20079061
Kwok, S. & Zhang, Y. Mixed aromatic-aliphatic organic nanoparticles as carriers of unidentified infrared emission features. Nature 479, 80–83 (2011).
pubmed: 22031328
doi: 10.1038/nature10542
Kwok, S., Volk, K. & Bernath, P. On the origin of infrared plateau features in Proto–Planetary Nebulae. Astrophys. J. 554, L87–L90 (2001).
doi: 10.1086/320913
Sloan, G. C. et al. The unusual hydrocarbon emission from the early carbon star HD 100764: the connection between aromatics and aliphatics. Astrophys. J. 664, 1144–1153 (2007).
doi: 10.1086/519236
Raponi, A. et al. Infrared detection of aliphatic organics on a cometary nucleus. Nat. Astron. 4, 500–505 (2020).
doi: 10.1038/s41550-019-0992-8
Pilorget, C. et al. First compositional analysis of Ryugu samples by the MicrOmega hyperspectral microscope. Nat. Astron. 6, 221–225 (2022).
doi: 10.1038/s41550-021-01549-z
Sandford, S. A. et al. Organics captured from Comet 81P/Wild 2 by the stardust spacecraft. Science 314, 1720–1724 (2006).
pubmed: 17170291
doi: 10.1126/science.1135841
Ito, M. et al. Hayabusa2 returned samples: a unique and pristine record of outer Solar System materials from asteroid Ryugu. Nat. Astron. 6, 1163–1171 (2022).
doi: 10.1038/s41550-022-01745-5
Tachibana, S. et al. Pebbles and sand on asteroid (162173) Ryugu: In situ observation and particles returned to Earth. Science 375, 1011–1016 (2022).
pubmed: 35143255
doi: 10.1126/science.abj8624
De Sanctis, M. C. et al. Localized aliphatic organic material on the surface of Ceres. Science 355, 719–722 (2017).
pubmed: 28209893
doi: 10.1126/science.aaj2305
Schuhmann, M. et al. Aliphatic and aromatic hydrocarbons in comet 67P/Churyumov-Gerasimenko seen by ROSINA. Astron. Astrophys. 630, A31 (2019).
Pizzarello, S., Yarnes, C. T. & Cooper, G. The Aguas Zarcas (CM2) meteorite: new insights into early solar system organic chemistry. Meteorit. Planet. Sci. 55, 1525–1538 (2020).
doi: 10.1111/maps.13532
Ito, M. et al. A pristine record of outer Solar System materials from asteroid Ryugu’s returned sample. Nat. Astron. 6, 1163–1171 (2022).
doi: 10.1038/s41550-022-01745-5
Dartois, E. et al. Chemical composition of carbonaceous asteroid Ryugu from synchrotron spectroscopy in the mid- to far-infrared of Hayabusa2-returned samples. Astron. Astrophys. 671, A2 (2023).
Yabuta, H. et al. Macromolecular organic matter in samples of the asteroid (162173) Ryugu. Science 379, eabn9057 (2024).
doi: 10.1126/science.abn9057
Studier, M. H., Hayatsu, R. & Anders, E. Origin of organic matter in early solar system—I. Hydrocarbons. Geochim. Cosmochim. Acta 32, 151–173 (1968).
doi: 10.1016/S0016-7037(68)80002-X
Sephton, M. A. Organic compounds in carbonaceous meteorites. Nat. Prod. Rep. 19, 292–311 (2002).
pubmed: 12137279
doi: 10.1039/b103775g
Navarro, V., van Spronsen, M. A. & Frenken, J. W. M. In situ observation of self-assembled hydrocarbon Fischer–Tropsch products on a cobalt catalyst. Nat. Chem. 8, 929 (2016).
pubmed: 27657868
doi: 10.1038/nchem.2613
Böller, B., Durner, K. M. & Wintterlin, J. The active sites of a working Fischer–Tropsch catalyst revealed by operando scanning tunnelling microscopy. Nat. Catal. 2, 1027–1034 (2019).
doi: 10.1038/s41929-019-0360-1
Llorca, J. & Casanova, I. Formation of carbides and hydrocarbons in chondritic interplanetary dust particles: a laboratory study. Meteorit. Planet. Sci. 33, 243–251 (1998).
doi: 10.1111/j.1945-5100.1998.tb01629.x
Kress, M. E. & Tielens, A. G. G. M. The role of Fischer-Tropsch catalysis in solar nebula chemistry. Meteorit. Planet. Sci. 36, 75–91 (2001).
doi: 10.1111/j.1945-5100.2001.tb01811.x
Ferrante, R. F., Moore, M. H., Nuth, J. A. & Smith, T. Laboratory studies of catalysis of CO to organics on grain analogs. Icarus 145, 297–300 (2000).
doi: 10.1006/icar.2000.6350
Sekine, Y. et al. An experimental study on Fischer-Tropsch catalysis: Implications for impact phenomena and nebular chemistry. Meteorit. Planet. Sci. 41, 715–729 (2006).
doi: 10.1111/j.1945-5100.2006.tb00987.x
Cabedo, V., Llorca, J., Trigo-Rodriguez, J. M. & Rimola, A. Study of Fischer–Tropsch-type reactions on chondritic meteorites. Astron. Astrophys. 650, A160 (2021).
Pareras, G., Cabedo, V., McCoustra, M. & Rimola, A. Single-atom catalysis in space: Computational exploration of Fischer–Tropsch reactions in astrophysical environments. Astron. Astrophys. 680, A57 (2023).
Abplanalp, M. J., Jones, B. M. & Kaiser, R. I. Untangling the methane chemistry in interstellar and solar system ices toward ionizing radiation: a combined infrared and reflectron time-of-flight analysis. Phys. Chem. Chem. Phys. 20, 5435–5468 (2018).
pubmed: 28972622
doi: 10.1039/C7CP05882A
Jones, B. M. & Kaiser, R. I. Application of reflectron time-of-flight mass spectroscopy in the analysis of astrophysically relevant ices exposed to ionization radiation: methane (CH4) and D4-methane (CD4) as a case study. J. Phys. Chem. Lett. 4, 1965–1971 (2013).
pubmed: 26283135
doi: 10.1021/jz400692r
Martínez, L. et al. Prevalence of non-aromatic carbonaceous molecules in the inner regions of circumstellar envelopes. Nat. Astron. 4, 97–105 (2020).
pubmed: 31934643
doi: 10.1038/s41550-019-0899-4
Martínez, L. et al. Metal-catalyst-free gas-phase synthesis of long-chain hydrocarbons. Nat. Commun. 12, 5937 (2021).
pubmed: 34642345
pmcid: 8511129
doi: 10.1038/s41467-021-26184-0
Accolla, M. et al. Silicon and hydrogen chemistry under laboratory conditions mimicking the atmosphere of evolved stars. Astrophys. J. 906, 44 (2021).
pubmed: 33594293
pmcid: 7116752
doi: 10.3847/1538-4357/abc703
Santoro, G. et al. The chemistry of cosmic dust analogs from C, C2, and C2H2 in C-rich circumstellar envelopes. Astrophys. J. 895, 97 (2020).
pubmed: 33154601
pmcid: 7116318
doi: 10.3847/1538-4357/ab9086
Merino, P. et al. Graphene etching on SiC grains as a path to interstellar polycyclic aromatic hydrocarbons formation. Nat. Commun. 5, 3054 (2014).
Hornekær, L. et al. Metastable structures and recombination pathways for atomic hydrogen on the graphite (0001) surface. Phys. Rev. Lett. 96, 156104 (2006).
pubmed: 16712173
doi: 10.1103/PhysRevLett.96.156104
Schulz, F. et al. Imaging Titan’s organic haze at atomic scale. Astrophys. J. 908, L13 (2021).
doi: 10.3847/2041-8213/abd93e
Zhong, D. et al. Linear alkane polymerization on a gold surface. Science 334, 213–216 (2011).
pubmed: 21998384
doi: 10.1126/science.1211836
Wang, S. et al. On-surface synthesis and characterization of individual polyacetylene chains. Nat. Chem. 11, 924–930 (2019).
pubmed: 31477850
doi: 10.1038/s41557-019-0316-8
Yamada, R. & Uosaki, K. Two-dimensional crystals of alkanes formed on Au(111) surface in neat liquid: structural investigation by scanning tunneling microscopy. J. Phys. Chem. B 104, 6021–6027 (2000).
doi: 10.1021/jp994061z
Zhang, H.-M., Xie, Z.-X., Mao, B.-W. & Xu, X. Self-assembly of normal alkanes on the Au (111) surfaces. Chem. A Eur. J. 10, 1415–1422 (2004).
doi: 10.1002/chem.200305334
Schuler, B., Meyer, G., Peña, D., Mullins, O. C. & Gross, L. Unraveling the molecular structures of asphaltenes by atomic force microscopy. J. Am. Chem. Soc. 137, 9870–9876 (2015).
pubmed: 26170086
doi: 10.1021/jacs.5b04056
Gross, L. et al. Organic structure determination using atomic-resolution scanning probe microscopy. Nat. Chem. 2, 821–825 (2010).
pubmed: 20861896
doi: 10.1038/nchem.765
Gross, L. et al. Bond-order discrimination by atomic force microscopy. Science 337, 1326–1329 (2012).
pubmed: 22984067
doi: 10.1126/science.1225621
Gross, L. et al. Atomic force microscopy for molecular structure elucidation. Angew. Chem. Int. Ed. 57, 3888–3908 (2018).
doi: 10.1002/anie.201703509
Schuler, B. et al. Characterizing aliphatic moieties in hydrocarbons with atomic force microscopy. Chem. Sci. 8, 2315–2320 (2017).
pubmed: 28451335
doi: 10.1039/C6SC04698C
Pavliček, N. et al. Polyyne formation via skeletal rearrangement induced by atomic manipulation. Nat. Chem. 10, 853–858 (2018).
pubmed: 29967394
pmcid: 6071858
doi: 10.1038/s41557-018-0067-y
Kaiser, K. et al. An sp-hybridized molecular carbon allotrope, cyclo[18]carbon. Science 365, 1299–1301 (2019).
pubmed: 31416933
doi: 10.1126/science.aay1914
Kaiser, K. et al. Visualization and identification of single meteoritic organic molecules by atomic force microscopy. Meteorit. Planet. Sci. 57, 644–656 (2022).
pubmed: 35912284
pmcid: 9305854
doi: 10.1111/maps.13784
Wetterer, S. M., Lavrich, D. J., Cummings, T., Bernasek, S. L. & Scoles, G. Energetics and kinetics of the physisorption of hydrocarbons on Au(111). J. Phys. Chem. B 102, 9266–9275 (1998).
doi: 10.1021/jp982338+
Kissin, Y. V. Hydrocarbon components in carbonaceous meteorites. Geochim. Cosmochim. Acta 67, 1723–1735 (2003).
doi: 10.1016/S0016-7037(02)00982-1
Zhao, L. et al. Pyrene synthesis in circumstellar envelopes and its role in the formation of 2D nanostructures. Nat. Astron. 2, 413–419 (2018).
doi: 10.1038/s41550-018-0399-y
Zhao, L. et al. Molecular mass growth through ring expansion in polycyclic aromatic hydrocarbons via radical–radical reactions. Nat. Commun. 10, 3689 (2019).
pubmed: 31417088
pmcid: 6695427
doi: 10.1038/s41467-019-11652-5
Ravagnan, L. et al. sp hybridization in free carbon nanoparticles—presence and stability observed by near edge X-ray absorption fine structure spectroscopy. Chem. Commun. 47, 2952–2954 (2011).
doi: 10.1039/c0cc03778h
Weijun, G. et al. Visualization of on-surface ethylene polymerization through ethylene insertion. Science 375, 1188–1191 (2022).
doi: 10.1126/science.abi4407
Hall, D. N. B. & Ridgway, S. T. Circumstellar methane in the infrared spectrum of IRC+10°216. Nature 273, 281–282 (1978).
doi: 10.1038/273281a0
Polehampton, E. T., Menten, K. M., Brünken, S., Winnewisser, G. & Baluteau, J.-P. Far-infrared detection of methylene. Astron. Astrophys. 431, 203–213 (2005).
doi: 10.1051/0004-6361:20041598
Berné, O. et al. Formation of the methyl cation by photochemistry in a protoplanetary disk. Nature 621, 56–59 (2023).
pubmed: 37364766
doi: 10.1038/s41586-023-06307-x
Agúndez, M., Martínez, J. I., de Andres, P. L., Cernicharo, J. & Martín-Gago, J. A. Chemical equilibrium in AGB atmospheres: successes, failures, and prospects for small molecules, clusters, and condensates. Astron. Astrophys. 637, A59. (2020).
pubmed: 32508346
pmcid: 7274841
doi: 10.1051/0004-6361/202037496
Cherchneff, I. The inner wind of IRC+10216 revisited: new exotic chemistry and diagnostic for dust condensation in carbon stars. Astron. Astrophys. 545, A12 (2012).
Agúndez, M., Roueff, E., Le Petit, F. & Le Bourlot, J. The chemistry of disks around T Tauri and Herbig Ae/Be stars. Astron. Astrophys. 616, A19 (2018).
pubmed: 30185991
pmcid: 6120683
doi: 10.1051/0004-6361/201732518
Chiar, J. E., Pendleton, Y. J., Geballe, T. R. & Tielens, A. G. G. M. Near‐infrared spectroscopy of the Proto–Planetary Nebula CRL 618 and the origin of the hydrocarbon dust component in the interstellar medium. Astrophys. J. 507, 281–286 (1998).
pubmed: 11542820
doi: 10.1086/306318
Goto, M. et al. Spatially resolved 3 micron spectroscopy of IRAS 22272+5435: formation and evolution of aliphatic hydrocarbon dust in proto–planetary nebulae. Astrophys. J. 589, 419–429 (2003).
doi: 10.1086/368018
Pilleri, P., Joblin, C., Boulanger, F. & Onaka, T. Mixed aliphatic and aromatic composition of evaporating very small grains in NGC 7023 revealed by the 3.4/3.3 μm ratio. Astron. Astrophys. 577, A16 (2015).
pubmed: 26594053
pmcid: 4650199
doi: 10.1051/0004-6361/201425590
Jones, A. P. et al. The evolution of amorphous hydrocarbons in the ISM: dust modelling from a new vantage point. Astron. Astrophys. 558 (2013).
Martínez, L. et al. Precisely controlled fabrication, manipulation and in-situ analysis of Cu based nanoparticles. Sci. Rep. 8, 7250 (2018).
pubmed: 29740027
pmcid: 5940906
doi: 10.1038/s41598-018-25472-y
Santoro, G. et al. INFRA-ICE: an ultra-high vacuum experimental station for laboratory astrochemistry. Rev. Sci. Instrum. 91, 124101 (2020).
pubmed: 33379937
doi: 10.1063/5.0027920
Andriamaharavo, N. R. Retention Data NIST Mass Spectrometry Data Center. Retrieved March 17, 2015 (NIST Mass Spectrometry Data Center, 2014).
Frisch, M. J. et al. Gaussian∼ 09 Revision D. 01. (Science Open, 2014).
Becke, A. D. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A 38, 3098–3100 (1988).
doi: 10.1103/PhysRevA.38.3098
Dunning, T. H. Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen. J. Chem. Phys. 90, 1007–1023 (1989).
doi: 10.1063/1.456153
Kardar, M. Statistical Physics of Particles (Cambridge University Press, 2007).
Peng, C. & Bernhard Schlegel, H. Combining synchronous transit and Quasi-Newton methods to find transition states. Isr. J. Chem. 33, 449–454 (1993).
doi: 10.1002/ijch.199300051
Krishnamurthy, R. V., Epstein, S., Cronin, J. R., Pizzarello, S. & Yuen, G. U. Isotopic and molecular analyses of hydrocarbons and monocarboxylic acids of the Murchison meteorite. Geochim. Cosmochim. Acta 56, 4045–4058 (1992).
pubmed: 11537206
doi: 10.1016/0016-7037(92)90015-B
Cronin, J. R. & Pizzarello, S. Aliphatic hydrocarbons of the Murchison meteorite. Geochim. Cosmochim. Acta 54, 2859–2868 (1990).
pubmed: 11537195
doi: 10.1016/0016-7037(90)90020-L