HCN dimers: iminoacetonitrile and N-cyanomethanimine

Evans, Richard A.; Lorencak, P.; Ha, T.‐K.; Wentrup, Curt

doi:10.1021/ja00019a026

Cited by 65 publications

(70 citation statements)

References 3 publications

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“…20 AMN, along with iminoacetonitrile, has received attention as an intermediate in the polymerization of hydrogen cyanide as well as a highly reactive synthon in heterocyclic organic synthesis. 7,11,13,[21][22][23] It is formally a trimer of hydrogen cyanide and spontaneously polymerizes when commercially available p-toluenesulfonate is neutralized (Figure 1b). 24 It allows easy access to HCN polymers under very mild and controllable conditions without the need to use HCN itself.…”

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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Section: Introductionmentioning

confidence: 99%

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

et al. 2015

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“…The structure of the resulting complex polymer is not determined, albeit several models for its structure have been proposed [24][25][26][27][28][29]. The large complex polymers consist mostly of H, C and N according to elemental analysis [27].…”

Section: Introductionmentioning

confidence: 99%

Navigating the Chemical Space of HCN Polymerization and Hydrolysis: Guiding Graph Grammars by Mass Spectrometry Data

Andersen

Flamm

et al. 2013

Entropy

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Polymers of hydrogen cyanide and their hydrolysis products constitute a plausible, but still poorly understood proposal for early prebiotic chemistry on Earth.HCN polymers are generated by the interplay of more than a dozen distinctive reaction mechanisms and form a highly complex mixture. Here we use a computational model based on graph grammars as a means of exploring the chemical spaces of HCN polymerization and hydrolysis. A fundamental issue is to understand the combinatorial explosion inherent in large, complex chemical systems. We demonstrate that experimental data, here obtained by mass spectrometry, and computationally predicted free energies together can be used

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“…The bands, which are growing at 2222, 1604, 1379 and 1218 cm −1 , correspond to the iminoacetonitrile, HN=CH=CN (Fig. 13) (Evans et al 1991). These assignments are also confirmed by the presence of bands at 2141 and 2063 cm −1 caused by the photodecomposition of iminoacetonitrile in cyanogen, NC-CN (Blanch & McCluskey 1995).…”

Section: Vuv Irradiationmentioning

confidence: 62%

Aminoacetonitrile characterization in astrophysical-like conditions

Borget

Danger

Duvernay

et al. 2012

A&A

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Context. Aminoacetonitrile (AAN) has been detected in 2008 in the hot core SgrB2. This molecule is of particular interest because it is a central molecule in the Strecker synthesis of amino acids. This molecule can be formed from methanimine (CH 2 NH), ammonia (NH 3 ) and hydrogen cyanide (HCN) in astrophysical icy conditions. Nevertheless, few studies exist about its infrared (IR) identification or its astrophysical characterization. Aims. We present in this study a characterization of the pure solid AAN and when it is diluted in water to study the influence of H 2 O on the main IR features of AAN. The reactivity with CO 2 and its photoreactivity are also studied and the main products were characterized. Methods. Fourier transformed infrared (FTIR) spectroscopy of AAN molecular ice was performed in the 10-300 K temperature range. We used temperature-programmed desorption coupled with mass spectrometry detection techniques to evaluate the desorption energy value. The influence of water was studied by quantitative FTIR spectroscopy and the main reaction and photochemical products were identified by FTIR spectroscopy. Results. We determined that in our experimental conditions, the IR limit of AAN detection in the water ice is about 1 × 10 16 molecule cm −2 , which means that the AAN detection is almost impossible within the icy mantle of interstellar grains. The desorption energy of pure solid AAN is of 63.7 kJ mol −1 with ν 0 to 10 28 molecule cm −2 s −1 , which implies that the presence of this molecule in the gas phase is only possible in hot cores. The glycine (Gly) formation from the AAN through the last step of the Strecker synthesis seems to be impossible in astrophysical-like conditions. Furthermore, AAN is photoresistant to vacuum ultra-violet radiation, which emphasizes the fact that AAN can be considered as a Gly reservoir molecule.

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HCN dimers: iminoacetonitrile and N-cyanomethanimine

Cited by 65 publications

References 3 publications

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

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

Navigating the Chemical Space of HCN Polymerization and Hydrolysis: Guiding Graph Grammars by Mass Spectrometry Data

Aminoacetonitrile characterization in astrophysical-like conditions

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