Simple Organics and Biomonomers Identified in HCN Polymers: An Overview
Abstract
:1. Introduction
2. Amino Acids
Compound | Starting material, c (M) | T (°C)/t/Catalyst | Final product analysed | Hydrolysis | Method of identification | Reference |
---|---|---|---|---|---|---|
Glycine | HCN, 0.2 | 100/1 d/- | Raw mixture | Acid | GC-MS | [75] |
NH4CN, 1 | 90/4 h/- | Brown precipitate | Acid | AAA | [76] | |
HCN, 1 | 90/4 h/NH4OH (pH 9.58) | Black solid | Acid | 2D-PC | [72] | |
HCN, 1.5 | 90/18 h/NH3 | Soluble oligomers | Acid | 2D-PC, AAA | [77] | |
HCN, 1.5 | 70/5 d/NH4OH | Soluble oligomers | Non hydrolysis | PC | [78] | |
HCN, 2.2 | 70/25 d/NH4OH | Soluble oligomers | Non hydrolysis | PC | [63] | |
NaCN, 1 | 38/3–30 d/NH4Cl | Black solid | Acid | GC-MS | [46] | |
HCN(L) | r.t./4 w/anhydrous NH3 | Dark solid residue | Acid | AAA | [51] | |
NaCN, 1 | r.t./3 m/pH 9.2 (HCl) | Soluble oligomers | Acid, basic and neutral | GC-MS | [79] | |
HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | AAA, GC-MS | [80,81] | |
HCN, 0.1 | r.t./4–12 m/NH4OH (pH 9.2) | Soluble oligomers | Acid and neutral | GC-MS | [82] | |
HCN, 0.1 | r.t./18 m/NH4OH (pH 9.2) | Soluble oligomers | Acid, Basic and neutral | GC-MS | [79] | |
HCN, 0.002–0.1 | r.t./UV radiation (Hg lamp)/pH (8–9) | Soluble oligomers | Acid | AAA | [69] | |
HCN(G) | r.t./UV radiation (Hg lamp) | Solid | Acid | AAA | [83] | |
HCN, 0.004–0.1 | r.t./γ-radiation (60Co source) | Raw mixture | Acid | PC, AAA, GC-MS | [84] | |
HCN, 0.1 | r.t./γ-radiation (60Co source)/pH 6 | Raw mixture | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t./γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [70] | |
NaCN, 0.1 | r.t./γ-radiation (60Co source)/pH 11.3 | Solution | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t.−40 °C/γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [71] | |
HCN, 1.5 | Refrigerator/4 d/NH3 | Black Solid | Acid | AAA | [51] | |
HCN, 0.1 | −20/2 m/NH3/pH 9.2 | Solution | Acid | HPLC | [67] | |
HCN, 0.1 | −20/25 y/NH3/pH 9.2 | Solution | Acid | HPLC | [67] | |
HCN, 0.1 | −78/25 y/NH3/pH 9.2 | Solution | Acid | HPLC | [67] | |
Glycinamide | HCN, 1.5 | 70/5 d/NH4OH | Soluble oligomers | Non hydrolysis | PC | [78] |
Aminomalonic acid | NaCN, 1 | 38/3–30 d/NH4Cl | Black solid | Acid | GC-MS | [46] |
Alanine | HCN, 1.5 | 100/1 d/- | Raw mixture | Acid | GC-MS | [75] |
NH4CN, 1 | 90/4 h/- | Brown precipitate | Acid | AAA | [76] | |
HCN, 1 | 90/4 h/NH4OH (pH 9.58) | Black solid | Acid | 2D-PC | [72] | |
HCN, 1.5 | 90/18 h/NH3 | Soluble oligomers | Acid | 2D-PC, AAA | [77] | |
HCN, 1.5 | 70/5 d/NH4OH | Soluble oligomers | Non hydrolysis- | PC | [78] | |
HCN, 2.2 | 70/25 d/NH4OH | Soluble oligomers | Non hydrolysis | PC | [63] | |
HCN(L) | r.t./4 w/anhydrous NH3 | Dark solid residue | Acid | AAA | [51] | |
NaCN, 1 | r.t./3 m/pH 9.2 (HCl) | Soluble oligomers | Acid, basic and neutral | GC-MS | [79] | |
HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | AAA, GC-MS | [80,81] | |
HCN, 0.1 | r.t./4–12 m/NH4OH (pH 9.2) | Soluble oligomers | Acid and neutral | GC-MS | [82] | |
HCN, 0.1 | r.t./18 m/NH4OH (pH 9.2) | Soluble oligomers | Acid, Basic and neutral | GC-MS | [79] | |
HCN, 0.002–0.1 | r.t./UV radiation (Hg lamp)/pH (8–9) | Solution | Acid | AAA | [69] | |
HCN(G) | r.t./UV radiation (Hg lamp) | Solid | Acid | AAA | [83] | |
HCN, 0.004–0.1 | r.t./γ-radiation (60Co source) | Raw mixture | Acid | PC, AAA, GC-MS | [84] | |
HCN, 0.1 | r.t./γ-radiation (60Co source)/pH 6 | Raw mixture | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t./γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [70] | |
NaCN, 0.1 | r.t./γ-radiation (60Co source)/pH 11.3 | Solution | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t.−40 °C/γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [71] | |
HCN, 1.5 | Refrigerator/4 d/NH3 | Black Solid | Acid | AAA | [51] | |
HCN, 0.1 | −20/2 m/NH3/pH 9.2 | Solution | Acid | HPLC | [67] | |
HCN, 0.1 | −20/25 y/NH3/pH 9.2 | Solution | Acid | HPLC | [67] | |
HCN, 0.1 | −78/25 y/NH3/pH 9.2 | Solution | Acid | HPLC | [67] | |
β-alanine | HCN, 1.5 | 90/18 h/NH3 | Soluble oligomers | Acid | 2D-PC, AAA | [77] |
HCN, 0.1 | r.t./4–12 m/NH4OH (pH 9.2) | Soluble oligomers | Acid and neutral | GC-MS | [82] | |
HCN, 0.1 | r.t./γ-radiation (60Co source)/pH 6 | Raw mixture | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t./γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [70] | |
NaCN, 0.1 | r.t./γ-radiation (60Co source)/pH 11.3 | Solution | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t.−40 °C/γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [71] | |
Sarcosine | HCN, 0.1 | r.t./γ-radiation (60Co source)/pH 6 | Raw mixture | Acid | AAA, GC-MS | [70] |
HCN, 0.1 | r.t./γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [70] | |
NaCN, 0.1 | r.t./γ-radiation (60Co source)/pH 11.3 | Solution | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t.−40 °C/γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [71] | |
Serine | NH4CN, 1 | 90/4 h/- | Brown precipitate | Acid | AAA | [76] |
HCN, 1 | 90/4 h/NH4OH (pH 9.58) | Black solid | Acid | 2D-PC | [72] | |
HCN, 1.5 | 90/18 h/NH3 | Soluble oligomers | Acid | 2D-PC, AAA | [77] | |
HCN(L) | r.t./.4 w/anhydrous NH3 | Dark solid residue | Acid | AAA | [51] | |
HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | AAA | [80,81] | |
HCN, 0.002–0.1 | r.t./UV radiation (Hg lamp)/pH (8–9) | Solution | Acid | AAA | [69] | |
HCN(G) | r.t./UV radiation (Hg lamp) | Solid | Acid | AAA | [83] | |
HCN, 0.004 | r.t./γ-radiation (60Co source) | Raw mixture | Acid | PC, AAA, GC-MS | [84] | |
HCN, 0.1 | r.t./γ-radiation (60Co source)/pH 6 | Raw mixture | Acid | AAA | [70] | |
HCN, 0.1 | r.t./γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA | [70] | |
NaCN, 0.1 | r.t./γ-radiation (60Co source)/pH 11.3 | Solution | Acid | AAA | [70] | |
HCN, 0.1 | r.t.−40 °C/γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [71] | |
HCN, 1.5 | Refrigerator/4 d/NH3 | Black Solid | Acid | AAA | [51] | |
2,3-Aminopropioinic acid | HCN, 1.5 | 90/18 h/NH3 | Soluble oligomers | Acid | 2D-PC, AAA | [77] |
Aspartic acid | HCN, 0.2 | 100/1 d/- | Raw mixture | Acid | GC-MS | [75] |
NH4CN, 1 | 90/4 h/- | Brown precipitate | Acid | AAA | [76] | |
HCN, 1 | 90/4 h/NH4OH (pH 9.58) | Black solid | Acid | 2D-PC | [72] | |
HCN, 1.5 | 90/18 h/NH3 | Soluble oligomers | Acid | 2D-PC, AAA | [77] | |
HCN, 1.5 | 70/5 d/NH4OH | Soluble oligomers | Non hydrolysis | PC | [78] | |
HCN, 2.2 | 70/25 d/NH4OH | Soluble oligomers | Non hydrolysis | PC | [63] | |
NaCN, 1 | 38/3–30 d/NH4Cl | Black solid | Acid | GC-MS | [46] | |
HCN(L) | r.t./4 w/anhydrous NH3 | Dark solid residue | Acid | AAA | [51] | |
NaCN, 1 | r.t./3 m/pH 9.2 (HCl) | Soluble oligomers | Acid, basic and neutral | GC-MS | [79] | |
HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | AAA, GC-MS | [80,81] | |
HCN, 0.1 | r.t./4–12 m/NH4OH (pH 9.2) | Soluble oligomers | Acid and neutral | GC-MS | [82] | |
HCN, 0.1 | r.t./18 m/NH4OH (pH 9.2) | Soluble oligomers | Acid, Basic and neutral | GC-MS | [79] | |
HCN, 0.002–0.1 | r.t./UV radiation (Hg lamp)/pH (8–9) | Solution | Acid | AAA | [69] | |
HCN(G) | r.t./UV radiation (Hg lamp) | Solid | Acid | AAA | [83] | |
HCN, 0.004–0.1 | r.t./γ-radiation (60Co source) | Raw mixture | Acid | PC, AAA, GC-MS | [84] | |
HCN, 0.1 | r.t./γ-radiation (60Co source)/pH 6 | Raw mixture | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t./γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [70] | |
NaCN, 0.1 | r.t./γ-radiation (60Co source)/pH 11.3 | Solution | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t.−40 °C/γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [71] | |
HCN, 1.5 | Refrigerator/4 d/NH3 | Black Solid | Acid | AAA | [51] | |
HCN, 0.1 | −20/2 m/NH3/pH 9.2 | Solution | Acid | HPLC | [67] | |
HCN, 0.1 | −20/25 y/NH3/pH 9.2 | Solution | Acid | HPLC | [67] | |
HCN, 0.1 | −78/25 y/NH3/pH 9.2 | Solution | Acid | HPLC | [67] | |
Diaminosuccinic acid | NaCN, 1 | r.t./3 m/pH 9.2 (HCl) | Soluble oligomers | Acid, basic and neutral | GC-MS | [79] |
HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | AAA, GC-MS | [80,81] | |
HCN, 0.1 | r.t./4–12 m/NH4OH (pH 9.2) | Soluble oligomers | Acid and neutral | GC-MS | [82] | |
HCN, 0.1 | r.t./18 m/NH4OH (pH 9.2) | Soluble oligomers | Acid, Basic and neutral | GC-MS | [79] | |
2-aminoisobutyric acid | HCN, 0.2 | 100/1 d/- | Raw mixture | Acid | GC-MS | [75] |
NaCN, 1 | r.t./3 m/pH 9.2 (HCl) | Soluble oligomers | Acid, basic and neutral | GC-MS | [79] | |
HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | GC-MS | [80,81] | |
HCN, 0.1 | r.t./4–12 m/NH4OH (pH 9.2) | Soluble oligomers | Acid and neutral | GC-MS | [82] | |
HCN, 0.1 | r.t./18 m/NH4OH (pH 9.2) | Soluble oligomers | Acid, Basic and neutral | GC-MS | [79] | |
2-amino-n-butyric acid | HCN, 1.5 | 90/18 h/NH3 | Soluble oligomers | Acid | 2D-PC, AAA | [77] |
HCN, 0.1 | r.t./γ-radiation (60Co source)/pH 6 | Raw mixture | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t./γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [70] | |
NaCN, 0.1 | r.t./γ-radiation (60Co source)/pH 11.3 | Solution | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t.−40 °C/γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [71] | |
4-amino-n-butyric acid | NH4CN, 1 | 90/4 h/- | Brown precipitate | Acid | AAA | [76] |
HCN, 1 | 90/4 h/NH4OH (pH 9.58) | Black solid | Acid | 2D-PC | [72] | |
Threonine | NH4CN, 1 | 90/4 h/- | Brown precipitate | Acid | AAA | [76] |
HCN, 1 | 90/4 h/NH4OH (pH 9.58) | Black solid | Acid | 2D-PC | [72] | |
HCN, 1.5 | 90/18 h/NH3 | Soluble oligomers | Acid | 2D-PC, AAA | [77] | |
HCN(L) | r.t./4 w/anhydrous NH3 | Dark solid residue | Acid | AAA | [51] | |
HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | AAA | [80,81] | |
HCN(G) | r.t./UV radiation (Hg lamp) | Solid | Acid | AAA | [83] | |
HCN, 0.004–0.1 | r.t./γ-radiation (60Co source) | Raw mixture | Acid | PC, AAA, GC-MS | [84] | |
HCN, 0.1 | r.t.−40 °C/γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [71] | |
HCN, 1.5 | Refrigerator/4 d/NH3 | Black Solid | Acid | AAA | [51] | |
Glutamic acid | HCN, 0.2 | 100/1 d/- | Raw mixture | Acid | GC-MS | [75] |
NH4CN, 1 | 90/4 h/- | Brown precipitate | Acid | AAA | [76] | |
HCN, 1.5 | 90/18 h/NH3 | Soluble oligomers | Acid | 2D-PC, AAA | [77] | |
HCN(L) | r.t./4 w/anhydrous NH3 | Dark solid residue | Acid | AAA | [51] | |
NaCN, 1 | r.t./3 m/pH 9.2 (HCl) | Soluble oligomers | Acid, basic and neutral | GC-MS | [79] | |
HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | AAA, GC-MS | [80,81] | |
HCN, 0.1 | r.t./18 m/NH4OH (pH 9.2) | Soluble oligomers | Acid, Basic and neutral | GC-MS | [79] | |
HCN(G) | r.t./UV radiation (Hg lamp) | Solid | Acid | AAA | [83] | |
HCN, 0.004–0.1 | r.t./γ-radiation (60Co source) | Raw mixture | Acid | PC, AAA, GC-MS | [84] | |
HCN, 0.1 | r.t./γ-radiation (60Co source)/pH 6 | Raw mixture | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t./γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [70] | |
NaCN, 0.1 | r.t./γ-radiation (60Co source)/pH 11.3 | Solution | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t.−40 °C/γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [71] | |
HCN, 1.5 | Refrigerator/4 d/NH3 | Black Solid | Acid | AAA | [51] | |
2-methyl aspartic acid | HCN, 0.1 | r.t./γ-radiation (60Co source)/pH 6 | Raw mixture | Acid | AAA, GC-MS | [70] |
HCN, 0.1 | r.t./γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [70] | |
NaCN, 0.1 | r.t./γ-radiation (60Co source)/pH 11.3 | Solution | Acid | AAA, GC-MS | [70] | |
HCN, 0.1 | r.t.−40 °C/γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [71] | |
Ornithine | NH4CN, 1 | 90/4 h/- | Brown precipitate | Acid | AAA | [76] |
HCN, 1 | 90/4 h/NH4OH (pH 9.58) | Black solid | Acid | 2D-PC | [72] | |
Histidine | NH4CN, 1 | 90/4 h/- | Brown precipitate | Acid | AAA | [76] |
HCN, 1 | 90/4 h/NH4OH (pH 9.58) | Black solid | Acid | 2D-PC | [72] | |
HCN(L) | r.t./4 w/anhydrous NH3 | Dark solid residue | Acid | AAA | [51] | |
HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | AAA | [80,81] | |
HCN(G) | r.t./UV radiation (Hg lamp) | Solid | Acid | AAA | [83] | |
HCN, 0.1 | r.t.−40 °C/γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [71] | |
HCN, 1.5 | Refrigerator/4 d/NH3 | Black Solid | Acid | AAA | [51] | |
Valine | HCN(L) | r.t./4 w/anhydrous NH3 | Dark solid residue | Acid | AAA | [51] |
HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | AAA | [80,81] | |
HCN(G) | r.t./UV radiation (Hg lamp) | Solid | Acid | AAA | [83] | |
HCN, 0.1 | r.t./γ-radiation (60Co source) | Raw mixture | Acid | PC, AAA, GC-MS | [84] | |
HCN, 1.5 | Refrigerator/4 d/NH3 | Black Solid | Acid | AAA | [51] | |
Isoleucine | HCN, 1.5 | 90/18 h/NH3 | Soluble oligomers | Acid | 2D-PC, AAA | [77] |
HCN (L) | r.t./4 w/anhydrous NH3 | Dark solid residue | Acid | AAA | [51] | |
NaCN, 1 | r.t./3 m/pH 9.2 (HCl) | Soluble oligomers | Acid, basic and neutral | GC-MS | [79] | |
HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | AAA, GC-MS | [80,81] | |
HCN, 0.1 | r.t./18 m/NH4OH (pH 9.2) | Soluble oligomers | Acid, Basic and neutral | GC-MS | [79] | |
HCN(G) | r.t./UV radiation (Hg lamp) | Solid | Acid | AAA | [83] | |
HCN, 1.5 | Refrigerator/4 d/NH3 | Black Solid | Acid | AAA | [51] | |
Leucine | HCN, 1.5 | 90/18 h/NH3 | Soluble oligomers | Acid | 2D-PC, AAA | [77] |
HCN (L) | r.t./4 w/anhydrous NH3 | Dark solid residue | Acid | AAA | [51] | |
HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | AAA | [80,81] | |
HCN(G) | r.t./UV radiation (Hg lamp) | Solid | Acid | AAA | [83] | |
HCN, 1.5 | Refrigerator/4 d/NH3 | Black Solid | Acid | AAA | [51] | |
Citrulline | HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | AAA | [80,81] |
HCN, 0.1 | r.t.−40 °C/γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [71] | |
Lysine | NH4CN, 1 | 90/4 h/- | Brown precipitate | Acid | AAA | [76] |
HCN, 1 | 90/4 h/NH4OH (pH 9.58) | Black solid | Acid | 2D-PC | [72] | |
HCN(L) | r.t./4 w/anhydrous NH3 | Dark solid residue | Acid | AAA | [51] | |
HCN, 0.1 | r.t./1–6 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | AAA | [80,81] | |
HCN(G) | r.t./UV radiation (Hg lamp) | Solid | Acid | AAA | [83] | |
HCN, 0.1 | r.t.−40 °C/γ-radiation (60Co source)/NH3/pH 9 | Solution | Acid | AAA, GC-MS | [71] | |
HCN, 1.5 | Refrigerator/4 d/NH3 | Black Solid | Acid | AAA | [51] | |
Arginine | HCN(L) | r.t./4 w/anhydrous NH3 | Dark solid residue | Acid | AAA | [51] |
HCN, 1.5 | Refrigerator/4 d/NH3 | Black Solid | Acid | AAA | [51] |
Hydantoins
3. Nucleic-Acid Bases
3.1. Purines
Compound | Starting material, c (M) | T (ºC)/t/Catalyser | Final product analysed | Hydrolysis | Yield (%) | Method of identification | Reference |
---|---|---|---|---|---|---|---|
Xhanthine | HCN, 0.1 | −78/27 y/NH3 (pH 9.2) | Solution + black solid | Acid | 0.022 | HPLC-UV, GC-MS | [66] |
Neutral | 0.022 | ||||||
Hypoxanthine | HCN, 1.5 | 90/18 h/NH3 | Solution + black solid | Acid | ~1 μmol/L | PC, UV-spectrum, PE | [77] |
NaCN, 1 | 38/3–30 d/NH4Cl | Black solid | Acid | D | GC-MS | [46] | |
HCN, 0.1 | −78/27 y/NH3 (pH 9.2) | Solution + black solid | Acid | 0.0041 | HPLC-UV, GC-MS | [66] | |
Neutral | 0.0058 | ||||||
Adenine | HCN, (s) | 90/24 h/NH4OH (1.5 M) | Solution | Acid | D | PC, UV-spectrum | [6] |
HCN, 1.5 | 90/18 h/NH3 | Solution + black solid | Acid | ~1 μmol/L | PC, UV-spectrum, PE | [77] | |
HCN, 9.9 | 90/8 d/NH4OH | Solution | Non hydrolysis | 60 mg/L | 2D-PC, UV-spectrum | [78] | |
HCN, 10 | 80/24 h/NH4OH | Solution | Acid | 0.027 | HPLC-UV | [99] | |
HCN, 1.5 | 70/2 d/NH4OH (3 M) | Solution | Non hydrolysis | D | 2D-PC, UV-spectrum | [78] | |
HCN, 11.1 | 70/5 d/NH4OH (12.8 M) | Solution | Non hydrolysis | 110 mg/L | 2D-PC, UV-spectrum | [78] | |
Acid | 700 mg/L | ||||||
NaCN, 1 | 38/3–30 d/NH4Cl | Black solid | Acid | D | GC-MS | [46] | |
HCN, 14.6 | r.t./26 h/NH4OH (7 M) | Solution | Non hydrolysis | D | 2D-PC, UV-spectrum | [78] | |
HCN, 8.25 | r.t./26 h/NH4OH (13 M) | Solution | Non hydrolysis | D | 2D-PC, UV-spectrum | [78] | |
HCN, 0.1 | r.t./1 w/NH4OH (pH 9.2) | Solution + black solid | Acid | 0.000013 | HPLC-UV, GC-MS | [66] | |
HCN, 0.1 | r.t./4 w/NH4OH (pH 9.2) | Solution + black solid | Acid | 0.00031 | HPLC-UV, GC-MS | [66] | |
HCN, 0.1 | r.t./8 w/NH4OH (pH 9.2) | Solution + black solid | Acid | 0.00062 | HPLC-UV, GC-MS | [66] | |
HCN, 0.1 | r.t./4–12 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | 0.003–0.004 | GC-MS | [82] | |
NaCN, 1 | r.t./1 y/pH 9.2 (HCl) | Soluble oligomers | Acid | D | TLC, UV-spectrum | [82] | |
NaCN, 2 (+HCOH) | r.t./9 m/pH 9.2 (HCl) | Non hydrolysis | 3 μmol/L | HPLC, UV spectrum, MS | [96] | ||
Neutral (2) | 0.06 | ||||||
HCN, 0.2 | r.t.−40 °C/γ-radiation/pH 6 | Solution | Acid (3) | t | HPLC, GC-MS | [97] | |
HCN, 0.01 (+glyconitrile) | −2/60 d/NH4OH (pH 9.2) | Solution | Acid (2) | 0.02 | HPLC-UV | [93] | |
HCN, 0.01 | −2/98 d/NH4OH (pH 9.2) | Solution | Acid (2) | 0.004 | HPLC-UV | [93] | |
HCN, 0.1 | −20/2 m/NH3 (pH 9.2) | Solution | Acid | 0.005 | HPLC-UV, ESI-MS | [67] | |
HCN, 0.001 | −20/3 m/NH4OH (pH 9.2) | Solution + black solid | Acid | 0.0042 | HPLC-UV, GC-MS | [66] | |
HCN, 0.01 | −20/3 m/NH4OH (pH 9.2) | Solution + black solid | Acid | 0.01 | HPLC-UV, GC-MS | [66] | |
HCN | −20/3 m/NH4OH (pH 9.2) | Solution + black solid | Acid | 0.0094 | HPLC-UV, GC-MS | [66] | |
HCN, 0.1 | −20/25 y/NH3 (pH 9.2) | Solution | Acid | 0.038 | HPLC-UV | [99] | |
HCN, 0.1 | −20/25 y/NH3 (pH 9.2) | Solution | Acid | 0.035 | HPLC-UV, ESI-MS | [67] | |
NaCN, 0.1 | −30/2 m/NH4Cl | Solution | Acid | 0.0004 | HPLC-UV | [99] | |
HCN, 0.1 | −78/25 y/NH3 (pH 9.2) | Solution | Acid | 0.04 | HPLC-UV, ESI-MS | [67] | |
HCN, 0.1 | −78/27 y/NH3 (pH 9.2) | Solution + black solid | Acid | 0.029 | HPLC-UV, GC-MS | [66] | |
Neutral | 0.012 | ||||||
Non hydrolysis | 0.00016 | ||||||
Guanine | HCN, 10 | 80/24 h/NH4OH | Solution | Acid | 0.0007 | HPLC-UV | [99] |
NaCN, 1 | 38/3–30 d/NH4Cl | Black solid | Acid | D | GC-MS | [46] | |
HCN, 0.1 | −20/25 y/NH3 (pH 9.2) | Solution | Acid | 0.0035 | HPLC-UV | [99] | |
HCN, 0.1 | −20/25 y/NH3 (pH 9.2) | Solution | Acid | 0.0004 | HPLC-UV, ESI-MS | [67] | |
NaCN, 0.1 | −30/2 m/NH4Cl | Solution | Acid | 0.000014 | HPLC-UV | [99] | |
HCN, 0.1 | −78/27 y/NH3 (pH 9.2) | Solution + black solid | Acid | 0.0067 | HPLC-UV, GC-MS | [66] | |
Neutral | 0.0033 | ||||||
Non hydrolysis | 0.00011 | ||||||
2,6-diaminopurine | HCN, 0.1 | −78/27 y/NH3 (pH 9.2) | Solution + black solid | Neutral | 0.0091 | HPLC-UV, GC-MS | [66] |
8-hydroxymethyladenine | NaCN, 2 (+HCOH) | r.t./9 m/pH 9.2 (HCl) | Non hydrolysis | 47 μmol/L | HPLC, UV spectrum, MS | [96] | |
Neutral (2)> | 0.06 |
3.2. Pyrimidines
Compound | Starting material, c(M) | T (ºC)/t/Catalyst | Final product analysed | Hydrolysis | Yield (%) | Method of identification | Reference |
---|---|---|---|---|---|---|---|
4,5-Dihydroxypyrimidine | HCN, 0.1 | r.t./4–12 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | 0.62 | TLC, UV spectrum | [102] |
HCN, 0.1 | r.t./4–12 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | 0.7–0.9 | GC-MS | [82] | |
NaCN, 1 | r.t./1 y/pH 9.2 (HCl) | Soluble oligomers | Acid | D | TLC, UV spectrum | [82] | |
HCN, 0.1 | −78/27 y/NH3 (pH 9.2) | Solution + black solid | Acid | 0.65 | HPLC-UV, GC-MS | [66] | |
Uracil | NaCN, 1 | 38/3–30 d/NH4Cl | Black solid | Acid | D | GC-MS | [46] |
HCN, 1 | r.t./6 m/NH4OH (pH 9.2) | Solution | Acid (2) | 0.001 | HPLC-UV | [103] | |
HCN, 0.1 | r.t./6 m/NH4OH (pH 9.2) | Solution | Acid (2) | 0.005 | HPLC-UV | [103] | |
NaCN, 1 | r.t./6 m/pH 9.2 (HCl) | Solution | Acid (2) | 0.001 | HPLC-UV | [103] | |
HCN, 0.1 | −78/27 y/NH3 (pH 9.2) | Solution + black solid | Acid | 0.00026 | HPLC-UV, GC-MS | [66] | |
Neutral | 0.0017 | ||||||
HCN, 0.2 | r.t.−40 °C/γ-rad (60Co)/pH 6 | Solution | Acid (3) | t | HPLC, GC-MS | [97] | |
5-Hydroxyuracil | NaCN, 1 | 38/3–30 d/NH4Cl | Black solid | Acid | D | GC-MS | [46] |
HCN, 0.1 | r.t./4–12 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | 0.002–0.004 | TLC, UV spectrum | [102] | |
HCN, 0.1 | r.t./4–12 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | 0.003 | GC-MS | [82] | |
HCN, 0.1 | −78/27 y/NH3 (pH 9.2) | Solution + black solid | Acid | 0.0015 | HPLC-UV, GC-MS | [66] | |
Cytosine | HCN, 0.2 | r.t.−40 °C/γ-rad (60Co)/pH 6 | Solution | Acid (3) | t | HPLC, GC-MS | [97] |
5-Aminouracil | NaCN, 1 | 38/3–30 d/NH4Cl | Black solid | Acid | D | GC-MS | [46] |
HCN, 0.1 | −78/27 y/NH3 (pH 9.2) | Solution + black solid | Acid | 0.0058 | HPLC-UV, GC-MS | [66] | |
Neutral | 0.0038 | ||||||
Orotic acid | NaCN, 1 | 38/3–30 d/NH4Cl | Black solid | Acid | D | GC-MS | [46] |
HCN, 0.1 | r.t./4–12 m/NH4OH (pH 9.2) | Soluble oligomers | Neutral (2) | 0.009 | TLC, UV spectrum | [102] | |
HCN, 0.1 | r.t./4–12 m/NH4OH (pH 9.2) | Soluble oligomers | Acid | 0.009 | GC-MS | [82] | |
HCN, 0.1 | −78/27 y/NH3 (pH 9.2) | Solution + black solid | Acid | 0.0025 | HPLC-UV, GC-MS | [66] | |
Neutral | 0.1 | ||||||
5-Aminoorotic acid | HCN, 0.1 | −78/27 y/NH3 (pH 9.2) | Solution + black solid | Neutral | 0.019 | HPLC-UV, GC-MS | [66] |
HCN, 0.1 | −78/27 y/NH3 (pH 9.2) | Solution + black solid | Non hydrolysis | 0.00028 | HPLC-UV, GC-MS | [66] | |
Thymine | HCN, 0.2 | r.t.−40 °C/γ-rad (60Co)/pH 6 | Solution | Acid (3) | t | HPLC, GC-MS | [97] |
1,2,5,6-Tetrahydropyrimidine | NaCN, 1 | 38/3–30 d/NH4Cl | Black solid | Acid | D | GC-MS | [46] |
4. Carboxylic Acids
5. Carbonyl Compounds
6. Pteridines
7. Others
8. Summary
Acknowledgments
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Ruiz-Bermejo, M.; Zorzano, M.-P.; Osuna-Esteban, S. Simple Organics and Biomonomers Identified in HCN Polymers: An Overview. Life 2013, 3, 421-448. https://doi.org/10.3390/life3030421
Ruiz-Bermejo M, Zorzano M-P, Osuna-Esteban S. Simple Organics and Biomonomers Identified in HCN Polymers: An Overview. Life. 2013; 3(3):421-448. https://doi.org/10.3390/life3030421
Chicago/Turabian StyleRuiz-Bermejo, Marta, María-Paz Zorzano, and Susana Osuna-Esteban. 2013. "Simple Organics and Biomonomers Identified in HCN Polymers: An Overview" Life 3, no. 3: 421-448. https://doi.org/10.3390/life3030421