Trinitromethane
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| Names | |
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| IUPAC name
Trinitromethane
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| Other names
Nitroform
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| Identifiers | |
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3D model (JSmol)
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| Properties | |
| CHN3O6 | |
| Molar mass | 151.04 g/mol |
| Appearance | Pale yellow crystals |
| Density | 1.469 g/cm3 |
| Melting point | 15 °C (59 °F; 288 K) |
| 44g/100ml at 20 °C | |
| Acidity (pKa) | 0.25 (see text) |
| Hazards | |
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| Related compounds | |
Related compounds
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Hexanitroethane Octanitropentane Tetranitromethane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Template:Chembox Footer/trackingTemplate:Short description
Trinitromethane, also referred to as nitroform, is a nitroalkane and oxidizer with chemical formula HC(NO2)3. It was first obtained in 1857 as the ammonium salt by the Russian chemist Leon Nikolaevich Shishkov (1830–1908).[2][3] In 1900, it was discovered that nitroform can be produced by the reaction of acetylene with anhydrous nitric acid.[4] This method went on to become the industrial process of choice during the 20th century. In the laboratory, nitroform can also be produced by hydrolysis of tetranitromethane under mild basic conditions.[5]
Acidity
Trinitromethane as a neutral molecule is colorless. It is highly acidic, easily forming an intensely yellow anion, (NO2)3C− (nitroformate). The pKa of trinitromethane has been measured at 0.17 ± 0.02 at 20 °C, which is remarkably acidic for a methane derivative.[6] Trinitromethane easily dissolves in water to form an acidic yellow solution.
There is some evidence that the anion, which obeys the 4n+2 Hückel rule, displays Y-aromaticity, a form of aromaticity disputed among chemists.[7]
Nitroform salts
Trinitromethane forms a series of bright yellow ionic salts. Many of these salts tend to be unstable and can be easily detonated by heat or impact.
The potassium salt of nitroform, KC(NO2)3 is a lemon yellow crystalline solid that decomposes slowly at room temperatures and explodes above 95 °C. The ammonium salt is somewhat more stable, and deflagrates or explodes above 200 °C. The hydrazine salt, hydrazinium nitroformate is thermally stable to above 125 °C and is being investigated as an ecologically friendly oxidizer for use in solid fuels for rockets.
Condensation with formaldehyde
As found by British chemists Hurd and Starke during WWII, trinitromethane reacts with paraformaldehyde, giving trinitroethanol.[8] This compound is a solvent to nitrocellulose and a precursor to high explosives such as trinitroethylorthoformate and trinitroethylorthocarbonate.
References
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- ^ Page Module:Citation/CS1/styles.css has no content.Budavari, Susan, ed. (1996). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.). Merck. ISBN 0911910123., 9859.
- ^ For biographical information about Leon Nikolaevich Shishkov, see The Free Dictionary
- ^ See:
- Page Module:Citation/CS1/styles.css has no content.Chichkoff, Léon (1857). "Note sur le nitroforme" [Note on nitroform]. Comptes rendus (in French). 45: 144–146.
{{cite journal}}: CS1 maint: unrecognized language (link) - Page Module:Citation/CS1/styles.css has no content.Schischkoff, L. (1857). "Ueber das Nitroform" [On nitroform]. Annalen der Chemie (in German). 103 (3): 364–366. doi:10.1002/jlac.18571030316. S2CID 97319556.
{{cite journal}}: CS1 maint: unrecognized language (link) - Abstracted in: Page Module:Citation/CS1/styles.css has no content.Schischkoff, L. (1857). "On nitroform". The Chemical Gazette. 15: 448.
- Abstracted in: Page Module:Citation/CS1/styles.css has no content.Schischkoff, L. (1858). "On nitroform". Philosophical Magazine. 4th series. 15: 302.
- Page Module:Citation/CS1/styles.css has no content.Chichkoff, Léon (1857). "Note sur le nitroforme" [Note on nitroform]. Comptes rendus (in French). 45: 144–146.
- ^ The Italian chemist Adolfo Baschieri discovered that nitroform (Italian: nitroformio) could be produced from acetylene (acetilene) and nitric acid (acido nitrico).
- Page Module:Citation/CS1/styles.css has no content.Baschieri, A. (1900). "Sul comportamento dell' acetilene con alcuni ossidanti" [On the behavior of acetylene with some oxidizers]. Atti della Reale Accademia dei Lincei. 5th series (in Italian). 9 (part I): 391–393.
{{cite journal}}: CS1 maint: unrecognized language (link) See p. 392. - Abstracted in German in: Page Module:Citation/CS1/styles.css has no content.Baschieri, A. (1900). "Über das Verhalten des Acetylens gegen einige Oxydationsmittel" [On the behavior of acetylene towards some oxidizers]. Chemisches Zentralblatt. 5th series (in German). 4 (part II): 528.
{{cite journal}}: CS1 maint: unrecognized language (link) - See also: Page Module:Citation/CS1/styles.css has no content.Nieuwland, Julius A.; Vogt, Richard R. (1945). The Chemistry of Acetylene. New York City, New York, USA: Reinhold Publishing Corp. p. 158.
- Page Module:Citation/CS1/styles.css has no content.Baschieri, A. (1900). "Sul comportamento dell' acetilene con alcuni ossidanti" [On the behavior of acetylene with some oxidizers]. Atti della Reale Accademia dei Lincei. 5th series (in Italian). 9 (part I): 391–393.
- ^ Page Module:Citation/CS1/styles.css has no content.Gakh, A. A.; Bryan, J. C.; Burnett, M. N.; Bonnesen, P. V. (2000). "Synthesis and structural analysis of some trinitromethanide salts". Journal of Molecular Structure. 520 (1–3): 221–228. Bibcode:2000JMoSt.520..221G. doi:10.1016/S0022-2860(99)00333-6.
- ^ Page Module:Citation/CS1/styles.css has no content.Novikov, S. S.; Slovetskii, V. I.; Shevelev, S. A.; Fainzilberg, A. A. (1962). "Spectrophotometric Determination of the Dissociation Constants of Aliphatic Nitro Compounds". Russian Chemical Bulletin. 11 (4): 552–559. doi:10.1007/BF00904751.
- ^ Page Module:Citation/CS1/styles.css has no content.Cioslowski, J.; Mixon, S. T.; Fleischmann, E. D. (1991). "Electronic structures of trifluoro-, tricyano-, and trinitromethane and their conjugate bases". Journal of the American Chemical Society. 113 (13): 4751–4755. Bibcode:1991JAChS.113.4751C. doi:10.1021/ja00013a007.
- ^ Page Module:Citation/CS1/styles.css has no content.British Abstracts: Series A. 1951.
Further reading
- Page Module:Citation/CS1/styles.css has no content.Schmidt, Eckart W. (2022). "Trinitromethane". Nitromethanes. Encyclopedia of Oxidizers. De Gruyter. pp. 2820–2832. doi:10.1515/9783110750294-022. ISBN 978-3-11-075029-4.
