Chemical evolution. IX. Mechanism of the oligomerization of hydrogen cyanide and its possible role in the origins of life
Abstract
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTChemical evolution. IX. Mechanism of the oligomerization of hydrogen cyanide and its possible role in the origins of lifeJ. P. Ferris, D. B. Donner, and W. LotzCite this: J. Am. Chem. Soc. 1972, 94, 20, 6968–6974Publication Date (Print):October 1, 1972Publication History Published online1 May 2002Published inissue 1 October 1972https://pubs.acs.org/doi/10.1021/ja00775a018https://doi.org/10.1021/ja00775a018research-articleACS PublicationsRequest reuse permissionsArticle Views293Altmetric-Citations50LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Hydrogen cyanide oligomers may have played a significant role in the synthesis of a wide range of prebiotic molecules.
“For example, hydrogen cyanide (HCN) oligomers may have played a significant role in the synthesis of a wide range of prebiotic molecules [122-126], and recently, dimeric forms of HCN (cyanomethanimine) [127] have been detected in the interstellar medium.”
From The future of quantum biology (2018) · cites this paper as [122]
Cited by
Sorted by citations
HCN and chemical evolution: The possible role of cyano compounds in prebiotic synthesis
Ferris, J. P., & Hagan, W. J. (1984) · Tetrahedron · doi:10.1016/s0040-4020(01)99315-9 · Cited by 354 · see citing works
Self-citationMarais, A., Adams, B., Ringsmuth, A. K., Ferretti, M., Gruber, J. M., Hendrikx, R., Schuld, M., Smith, S. L., Sinayskiy, I., Krüger, T. P. J., et al. (2018) · Journal of The Royal Society Interface · doi:10.1098/rsif.2018.0640 · Cited by 274 · see citing works
Senanayake, S. D., & Idriss, H. (2006) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0505768103 · Cited by 123 · see citing works
Minard, R. D., Hatcher, P. G., Gourley, R. C., & Matthews, C. N. (1998) · Origins of Life and Evolution of Biospheres · doi:10.1023/a:1006566125815 · Cited by 70 · see citing works
Origins of Life: The Primal Self-Organization
Egel, R., Mulkidjanian, A. Y., & Lankenau, D. (2011) · Springer eBooks · doi:10.1007/978-3-642-21625-1 · Cited by 66 · see citing works
Saladino, R., Crestini, C., Costanzo, G., & DiMauro, E. (2005) · Springer eBooks · doi:10.1007/b136152 · Cited by 59 · see citing works
Šponer, J. E., Szabla, R., Góra, R., Saitta, A. M., Pietrucci, F., Saija, F., di Mauro, E., Saladino, R., Ferus, M., Civiš, S., et al. (2016) · Physical Chemistry, Chemical Physics - PCCP · doi:10.1039/c6cp00670a · Cited by 46 · see citing works
The Possible Role of Volcanic Aquifers in Prebiologic Genesis of Organic Compounds and RNA
Washington, J. W. (2000) · Origins of Life and Evolution of Biospheres · doi:10.1023/a:1006692606492 · Cited by 59 · see citing works
“AICN has been formed from reaction of diaminomaleonitrile ((CN)2C2(NH2)2) and formamide (HCONH2) (Ferris et al., 1972), both of which are produced in condensation of HCN solutions (Ferris, 1992; Ferris et al., 1972; Oro and Kimball, 1962).”
BackgroundXiang, Y., Drenkard, S., Baumann, K., Hickey, D., & Eschenmoser, A. (1994) · Helvetica Chimica Acta · doi:10.1002/hlca.19940770814 · Cited by 52 · see citing works
Ferris, J. P., Donner, D. B., & Lobo, A. P. (1973) · Journal of Molecular Biology · doi:10.1016/0022-2836(73)90042-9 · Cited by 48 · see citing works
Self-citationSynthesis of porphyrazine-octaamine, hexamine and diamine derivatives
Fuchter, M. J., Beall, L. S., Baum, S. M., et al. (2005) · Tetrahedron · doi:10.1016/j.tet.2005.03.090 · Cited by 47 · see citing works
Chemical evolution toward the origin of life
Fitz, D., Reiner, H., & Rode, B. M. (2007) · Pure and Applied Chemistry · doi:10.1351/pac200779122101 · Cited by 40 · see citing works
A Dimer of Hydrogen Cyanide Stabilized by a Lewis Acid
Bläsing, K., Bresien, J., Labbow, R., Schulz, A., & Villinger, A. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201804193 · Cited by 32 · see citing works
Molecular simulations for the spectroscopic detection of atmospheric gases
Sousa-Silva, C., Petkowski, J. J., & Seager, S. (2019) · Physical Chemistry Chemical Physics · doi:10.1039/c8cp07057a · Cited by 31 · see citing works
Ferris, J. P., Donner, D. B., & Lobo, A. P. (1973) · Journal of Molecular Biology · doi:10.1016/0022-2836(73)90043-0 · Cited by 30 · see citing works
Self-citationPossible precursors in HCN oligomerization
Clemmons, J. H., Jasien, P. G., & Dykstra, C. E. (1983) · Molecular Physics · doi:10.1080/00268978300100461 · Cited by 30 · see citing works
HCN Did Not Condense to Give Heteropolypeptides on the Primitive Earth
Ferris, J. P. (1979) · Science · doi:10.1126/science.218287 · Cited by 30 · see citing works
Self-citationSandström, H., & Rahm, M. (2021) · ACS Earth and Space Chemistry · doi:10.1021/acsearthspacechem.1c00195 · Cited by 29 · see citing works
Tetracyanomanganate(II) and Its Salts of Divalent First-Row Transition Metal Ions
Manson, J. L., Buschmann, W. E., & Miller, J. S. (2001) · Inorganic Chemistry · doi:10.1021/ic0012726 · Cited by 27 · see citing works
The preparation of dicyano-1,3,4-thiadiazole and tricyanothiazole via 1,2,3-dithiazole chemistry
Christoforou, I. C., Kalogirou, A. S., & Koutentis, P. A. (2009) · Tetrahedron · doi:10.1016/j.tet.2009.10.003 · Cited by 24 · see citing works
Microwave spectra, dipole moments, and energy difference of E and Z C-cyanomethanimine (HCN dimer)
Takano, S., Sugié, M., Sugawara, K.-I., et al. (1990) · Journal of Molecular Spectroscopy · doi:10.1016/0022-2852(90)90273-s · Cited by 24 · see citing works
Chemical evolution XXIX. Pyrimidines from hydrogen cyanide
Ferris, J. P., Joshi, P. C., & Lawless, J. (1977) · Biosystems · doi:10.1016/0303-2647(77)90015-6 · Cited by 23 · see citing works
Self-citationFerris, J. P., Wos, J. D., Ryan, T. J., Lobo, A. P., & Donner, D. B. (1974) · Origins of Life and Evolution of Biospheres · doi:10.1007/bf00927020 · Cited by 23 · see citing works
Self-citationCharacterization of HCN-Derived Thermal Polymer: Implications for Chemical Evolution
Villafañe-Barajas, S. A., Ruiz‐Bermejo, M., Rayo-Pizarroso, P., & Colín-García, M. (2020) · Processes · doi:10.3390/pr8080968 · Cited by 21 · see citing works
Leśniak, S., Chrostowska, A., Kuc, D., et al. (2009) · Tetrahedron · doi:10.1016/j.tet.2009.10.080 · Cited by 17 · see citing works
A theoretical study of the reactive dimerization of HCN
MOFFAT, J. B., & Tang, K. F. (1976) · Journal of Theoretical Biology · doi:10.1016/0022-5193(76)90140-5 · Cited by 16 · see citing works
Stabilisierung eines Blausäure‐Dimers mit einer Lewis‐Säure
Bläsing, K., Bresien, J., Labbow, R., Schulz, A., & Villinger, A. (2018) · Angewandte Chemie · doi:10.1002/ange.201804193 · Cited by 15 · see citing works
Villafañe-Barajas, S. A., Ruiz‐Bermejo, M., Rayo-Pizarroso, P., Gálvez, S., Mateo‐Martí, E., & Colín-García, M. (2021) · Life · doi:10.3390/life11070661 · Cited by 12 · see citing works
Zaia, D. A. M., & Zaia, C. T. B. V. (2020) · Symmetry · doi:10.3390/sym12122046 · Cited by 11 · see citing works
Chrostowska, A., Dargelos, A., Graciaa, A., et al. (2009) · Tetrahedron · doi:10.1016/j.tet.2009.09.008 · Cited by 11 · see citing works
Response : HCN Did Not Condense to Give Heteropolypeptides on the Primitive Earth
Matthews, C. N. (1979) · Science · doi:10.1126/science.203.4385.1136 · Cited by 11 · see citing works
Pyrolysis of amines: Infrared spectrum of C-cyanomethanimine
Hamada, Y., Tsuboi, M., Nakanaga, T., et al. (1986) · Journal of Molecular Spectroscopy · doi:10.1016/0022-2852(86)90156-6 · Cited by 10 · see citing works
Freeman, F., & Gomarooni, M. (2006) · International Journal of Quantum Chemistry · doi:10.1002/qua.21024 · Cited by 9 · see citing works
Reflectance spectra of Titan tholin between 7000 and 10 cm-1
Brucato, J. R., Migliorini, A., Barucci, M. A., et al. (2010) · Astronomy and Astrophysics · doi:10.1051/0004-6361/200912054 · Cited by 9 · see citing works
“…physical-chemical conditions able to process materials that are suitable for the synthesis of nucleic acid bases which were used in the form of analogues in laboratory as macromolecular precursors of both purine and pyrimidine derivatives upon acidic or basic hydrolysis (Ferris et al. 1972).”
BackgroundSpectroscopic Study on the Pyrolytic Products of Amines
Hamada, Y., & Takeo, H. (1992) · Applied Spectroscopy Reviews · doi:10.1080/05704929208021757 · Cited by 8 · see citing works
A Thermodynamic Landscape of Hydrogen Cyanide-Derived Molecules and Polymers
Sandström, H., Izquierdo‐Ruiz, F., Cappelletti, M., Dogan, R., Sharma, S., Bailey, C., & Rahm, M. (2024) · ACS Earth and Space Chemistry · doi:10.1021/acsearthspacechem.4c00088 · Cited by 7 · see citing works
Study of Ferrocyanide Adsorption onto Different Minerals as Prebiotic Chemistry Assays
Samulewski, R. B., Pintor, B. E., Ivashita, F. F., Paesano, A., & Zaia, D. A. M. (2021) · Astrobiology · doi:10.1089/ast.2020.2322 · Cited by 7 · see citing works
“However, the experiments carried out with cyanide employ a much higher concentration than would have existed in the prebiotic sea of Earth (Oro´, 1960; Ferris et al., 1972; Ferris and Edelson, 1978; Stribling and Miller, 1987).”
Perosa, A., Selva, M., & Tundo, P. (1999) · Journal of the Chemical Society Perkin Transactions 2 · doi:10.1039/a905563k · Cited by 7 · see citing works
Ayachi, H., Gazzeh, H., Boubaker, T., et al. (2023) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.2c02493 · Cited by 6 · see citing works
Fitz, D., Jakschitz, T. A. E., & Rode, B. M. (2011) · Springer eBooks · doi:10.1007/978-3-642-21625-1_5 · Cited by 6 · see citing works
Chemical evolution and the origin of life
West, M. W., Koch, R. A., & Chang, S. (1978) · Origins of Life and Evolution of Biospheres · doi:10.1007/bf00929715 · Cited by 5 · see citing works
Loew, G. H., & Chang, S. (1975) · Origins of Life and Evolution of Biospheres · doi:10.1007/bf01372396 · Cited by 4 · see citing works
Loew, G. H., & Chang, S. (1974) · Journal of Molecular Evolution · doi:10.1007/bf01797454 · Cited by 4 · see citing works
Chemical evolution and the origin of life
West, M. W., Gill, E. D., Sherwood, B., & Kvenvolden, K. A. (1974) · Origins of Life and Evolution of Biospheres · doi:10.1007/bf01207650 · Cited by 4 · see citing works
The photolysis of α-azidonitriles
Barone, A. D., & Watt, D. S. (1978) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)95026-9 · Cited by 3 · see citing works
How Does Adenine Form from Hydrogen Cyanide?
Cappelletti, M., & Rahm, M. (2026) · Journal of the American Chemical Society · doi:10.1021/jacs.5c09522 · Cited by 2 · see citing works
The Effects of Iron on In Silico Simulated Abiotic Reaction Networks
Shahi, S. R., & Cleaves, H. J. (2022) · Molecules · doi:10.3390/molecules27248870 · Cited by 2 · see citing works
Schwarze, T., Sperlich, E., Müller, T., et al. (2021) · Helvetica Chimica Acta · doi:10.1002/hlca.202100028 · Cited by 2 · see citing works
Field-Theodore, T. E., Ravasio, M., Alessandrini, S., Carlo, C., & Puzzarini, C. (2025) · The Astrophysical Journal · doi:10.3847/1538-4357/ae058d · Cited by 1 · see citing works
“…not only in solution, but also in the solid ( ice ) phase; a variety of prebiotic biomolecules are, of course, produced via the oligomerization of HCN under appropriate conditions ( H. Wakamatsu et al. 1966; J. P. Ferris et al. 1972a, 1972b; M. Ruiz-Bermejo et al. 2013; M. Yadav et al. 2020 ) .”
Ferris, J. P., Wos, J. D., Ryan, T. J., Lobo, A. P., & Donner, D. B. (1974) · Springer eBooks · doi:10.1007/978-94-010-2239-2_12 · Cited by 1 · see citing works
Self-citationThe Role of Formamide in Prebiotic Chemistry
Saladino, R., Costanzo, G., & Bizzarri, B. M. (2023) · Wiley eBooks · doi:10.1002/9781394264155.ch3 · Cited by 2 · see citing works
Dimerization of an N-alkylformimidoyl cyanide
Kooi, J., & Boyer, J. H. (1975) · Bioorganic Chemistry · doi:10.1016/0045-2068(75)90051-6
Neuere Erkenntnisse zur Polymerisation von Blausäure
Lotz, W., Donner, D. B., & Ferris, J. P. (1974) · Die Makromolekulare Chemie · doi:10.1002/macp.1974.021750205
Self-citationFerris, J. P., Donner, D. B., & Lotz, W. (1972) · ChemInform · doi:10.1002/chin.197250115
Self-citation(1996) · The chemistry of heterocyclic compounds/The Chemistry of heterocyclic compounds · doi:10.1002/9780470187944.refs
Ferris, J. P., Wos, J. D., Ryan, T. J., Lobo, A. P., & Donner, D. B. (1974) · Springer eBooks · doi:10.1007/978-94-015-1118-6_11
Self-citationLoew, G. H., & Chang, S. (1974) · Springer eBooks · doi:10.1007/978-94-010-2282-8_13
- Authors
- Ferris, J. P., Donner, D. B., & Lotz, W.
- ORCID
- Donner, D. B.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1972-10
- Volume
- 94
- Issue
- 20
- Pages
- 6968-6974
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1965506450
- Cited by
- 57
- References
- 0
- Citations by year
- 2026: 1 · 2025: 1 · 2024: 1 · 2023: 2 · 2022: 1 · 2021: 4 · 2020: 2 · 2019: 1 · 2018: 3 · 2016: 1
- FWCI
- 6.44
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Astrophysics and Star Formation Studies
- Keywords
- hydrogen cyanide, oligomerization, reaction mechanism, origin of life, chemical evolution, prebiotic chemistry, amino acid precursors
- MeSH terms
- Amino Acids, Biology, Cyanides, Hydrogen, Peptides, Photochemistry
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
