Studies on the structure of HCN oligomers

Umemoto, Kimiko; Takahasi, Makoto; Yokota, Kazumichi

doi:10.1007/bf02386468

Cited by 38 publications

(35 citation statements)

References 11 publications

(5 reference statements)

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“…Quirico et al [8] reported an IR spectrum of an HCN polymer prepared from pure NH 3 and liquid HCN that was similar to the IR spectrum in this study. Similar IR data were reported by Liebman et al [26] and Umemoto et al [16] for HCN polymers obtained from liquid HCN and Et 3 N in MeCN, and from gaseous HCN and aqueous NH 3 , respectively. The IR spectra do not provide sufficient information to identify the , N¼NÀO antisym.…”

supporting

confidence: 85%

New Insights into the Characterization of ‘Insoluble Black HCN Polymers’

Ruíz-Bermejo

Fuente

Rogero

et al. 2012

Chemistry & Biodiversity

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The data presented here provide a novel contribution to the understanding of the structural features of HCN polymers and could be useful in further development of models for prebiotic chemistry. The interpretation of spectroscopic and analytical data, along with previous results reported by other authors, allowed us to propose a mechanism for the aqueous polymerization of HCN from its primary and simplest isolated oligomer, the diaminomaleonitrile (DAMN) tetramer. We suggest that 'insoluble black HCN polymers' are formed by an unsaturated complex matrix, which retains a significant amount of H(2) O and important bioorganic compounds or their precursors. This polymeric matrix can be formed by various motifs of imidazoles and cyclic amides, among others. The robust formation of HCN polymers assayed under several conditions seems to explain the plausible ubiquity of these complex substances in space.

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supporting

confidence: 85%

New Insights into the Characterization of ‘Insoluble Black HCN Polymers’

Ruíz-Bermejo

Fuente

Rogero

et al. 2012

Chemistry & Biodiversity

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“…Hydrolysis experiments of the polymers result in the observation of amino acids with particularly significant amounts of glycine and polycyclic nitrogenous compounds such as purines and imidazole derivatives (Supplementary Figure S1). 9,11,[24][25][26][27][28][29][30] Because of these properties, we investigated the AMN polymer as a candidate for a new generic coating method that may be particularly useful in biomedical applications such as cell culture tools, providing high cell attachment and surface coatings on implantable medical devices providing enhanced tissue integration.…”

Section: Introductionmentioning

confidence: 99%

Prebiotic-chemistry inspired polymer coatings for biomedical and material science applications

et al. 2015

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In the field of prebiotic chemistry, hydrogen cyanide (HCN)-derived polymers have been studied for many years as a possible source of the precursors that provide the building blocks for proteins as well as nucleic acids, and they have also been associated with the origin of life. The HCN trimer, aminomalononitrile (AMN), polymerizes to give a brown complex nitrogenous polymer. We report the one-step polymerization-deposition of AMN as a simple generic surface-coating method and as an application of prebiotic chemical research to material science. We found that this polymerization, carried out in buffered aqueous solutions, can be used to coat a wide range of organic and inorganic substrate materials. The robust, non-cytotoxic coatings also provide for excellent cell attachment, suggesting potential biomedical applications. Furthermore, the coating chemistry allows for the immobilization of other compounds, including metals, both during coating formation or by performing secondary immobilization reactions.

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“…However, the structures of these polymers remain unknown despite extensive effort. [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] Figures 1 and 2 show the proposed polymer structures. The "ladder" structures in Fig.…”

Section: Introductionmentioning

confidence: 99%

“…1 comprise repeats of the HCN dimer; the original trans form was originally suggested by Volker 11 ͓Fig. 1͑a͔͒ and the cis variation was subsequently offered by Umemoto et al 12 ͓Fig. 1͑b͔͒.…”

Section: Introductionmentioning

confidence: 99%

HCN polymers characterized by solid state NMR: Chains and sheets formed in the neat liquid

Mamajanov

Herzfeld

2009

The Journal of Chemical Physics

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Hydrogen cyanide polymerizes readily under a variety of conditions and significant prebiotic roles have been suggested for these polymers due to the abundance of HCN in universe. However, the structures of HCN polymers have been more speculative than grounded in experimental data. Here we show that 13 C and 15 N solid state NMR spectra of polymers formed in neat HCN are inconsistent with the previously proposed structures and suggest instead that the polymers are formed by simple monomer addition, first in head-to-tail fashion to form linear, conjugated chains, and then laterally to form saturated two-dimensional networks. This interpretation of the NMR spectra finds support in other information about the polymerization of neat HCN, including the presence of free radicals. As expected from the literature, formation of the HCN tetramer, diaminomaleonitrile, is also observed, but only when the reaction is catalyzed exclusively by base and then in crystalline form.

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Studies on the structure of HCN oligomers

Cited by 38 publications

References 11 publications

New Insights into the Characterization of ‘Insoluble Black HCN Polymers’

New Insights into the Characterization of ‘Insoluble Black HCN Polymers’

Prebiotic-chemistry inspired polymer coatings for biomedical and material science applications

HCN polymers characterized by solid state NMR: Chains and sheets formed in the neat liquid

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