Trinitromethane

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 (1830–1908).See:

• Abstracted in:
• Abstracted in: In 1900, it was discovered that nitroform can be produced by the reaction of acetylene with anhydrous nitric acid.The Italian chemist Adolfo Baschieri discovered that nitroform (Italian: nitroformio) could be produced from acetylene (acetilene) and nitric acid (acido nitrico).
• See p. 392.
• Abstracted in German in:
• See also: 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.

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. 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.

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 . This compound is a solvent to nitrocellulose and a precursor to high explosives such as trinitroethylorthoformate and trinitroethylorthocarbonate.

References

References

1. {{Merck12th
2. For biographical information about Leon Nikolaevich Shishkov, see [https://encyclopedia2.thefreedictionary.com/Leon+Nikolaevich+Shishkov The Free Dictionary]
3. (2000). "Synthesis and structural analysis of some trinitromethanide salts". Journal of Molecular Structure.
4. (1962). "Spectrophotometric Determination of the Dissociation Constants of Aliphatic Nitro Compounds". Russian Chemical Bulletin.
5. (1991). "Electronic structures of trifluoro-, tricyano-, and trinitromethane and their conjugate bases". Journal of the American Chemical Society.
6. (1951). "British Abstracts: Series A.".