Utente:Grasso Luigi/sanbox1/Trinitrometano
| Trinitrometano | |
|---|---|
 | |
| Nome IUPAC | |
| Trinitrometano [1][2][3][4] | |
| Nomi alternativi | |
| nitroformio | |
| Caratteristiche generali | |
| Formula bruta o molecolare | CHN3O6 |
| Massa molecolare (u) | 151.04 [5] |
| Aspetto | Cristalli giallo pallido |
| Numero CAS | |
| SMILES | C([N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-] |
| Proprietà chimico-fisiche | |
| Densità (g/cm3, in c.s.) | 1.469 |
| Solubilità in acqua | 44g/100ml (20°C)[6] |
| Temperatura di fusione | 15 |
| Tensione di vapore (Pa) a 295 K | 19 mmHg (20°C)[6] |
| Dati farmacologici | |
| Categoria farmacoterapeutica | antibiotici, tetracicline |
| Modalità di somministrazione | orale |
| Indicazioni di sicurezza | |
| Simboli di rischio chimico | |
 
| |
| attenzione | |
| Frasi H | --- |
| Consigli P | ---[7]---[8] |
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).[9][10] In 1900, it was discovered that nitroform can be produced by the reaction of acetylene with anhydrous nitric acid.[11] 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.[12]
Acidità[modifica | modifica wikitesto]
Trinitromethane as a neutral molecule is colorless. It is highly acidic, easily forming an intensely yellow anion, (NO2)3C−. The pKa of trinitromethane has been measured at 0.17 ± 0.02 at 20 °C, which is remarkably acidic for a methane derivative.[13] 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, is aromatic.[14]
Composti[modifica | modifica wikitesto]
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.
Note[modifica | modifica wikitesto]
- ^ (EN) Favre Henri A. e Powell Warren H. (a cura di), Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013, IUPAC Chemical Nomenclature and Structure Representation Division, Londra, IUPAC/RSC, 2013, ISBN 978-0-85404-182-4.
- ^ (EN) PubChem Compound, AC1L1C0X - Compound Summary, su pubchem.ncbi.nlm.nih.gov, National Center for Biotechnology Information, 25 Marzo 2005. URL consultato il 13 Ottobre 2011.
- ^ (EN) Chemical Entities of Biological Interest, methanediyl (CHEBI:29357), su ebi.ac.uk, EBI (UK), 14-01-2009. URL consultato il 02-01-2012.
- ^ Susan Budavari (a cura di), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 12ª ed., Whitehouse St (New Jersey, USA), Merck & Co., 1996, ISBN 0911910123.
- ^ (EN) IUPAC Commission on Isotopic Abundances and Atomic Weights., Atomic weights of the elements 2017, su Queen Mary University of London.
- ^ a b (EN) NIOSH Pocket Guide to Chemical Hazards, 1,1,2-Trichloroethane, su cdc.gov, NIOSH.
- ^ Scheda del composto su IFA-GESTIS
- ^ Scheda del composto su ARPA
- ^ For biographical information about Leon Nikolaevich Shishkov, see The Free Dictionary
- ^ See:
- (French) Note sur le nitroforme, in Comptes rendus, vol. 45, 1857, pp. 144–146. Lingua sconosciuta: French (aiuto)
- (German) Ueber das Nitroform, in Annalen der Chemie, vol. 103, n. 3, 1857, pp. 364–366, DOI:10.1002/jlac.18571030316. Lingua sconosciuta: German (aiuto)
- Abstracted in: On nitroform, in The Chemical Gazette, vol. 15, 1857.
- Abstracted in: On nitroform, in Philosophical Magazine, vol. 15, 1858.
- ^ The Italian chemist Adolfo Baschieri discovered that nitroform (Italian: nitroformio) could be produced from acetylene (acetilene) and nitric acid (acido nitrico).
- (Italian) Sul comportamento dell' acetilene con alcuni ossidanti, in Atti della Reale Accademia dei Lincei, 9 (part I), 1900, pp. 391–393. Lingua sconosciuta: Italian (aiuto) See p. 392.
- Abstracted in German in: (German) Über das Verhalten des Acetylens gegen einige Oxydationsmittel, in Chemisches Central-blatt, 4 (part II), 1900. Lingua sconosciuta: German (aiuto)
- See also: The Chemistry of Acetylene, New York City, New York, USA, Reinhold Publishing Corp., 1945, 158.
- ^ Synthesis and structural analysis of some trinitromethanide salts (PDF), in Journal of Molecular Structure, vol. 520, 1–3, 2000, pp. 221–228, DOI:10.1016/S0022-2860(99)00333-6.
- ^ Spectrophotometric Determination of the Dissociation Constants of Aliphatic Nitro Compounds, in Russian Chemical Bulletin, vol. 11, n. 4, 1962, pp. 552–559, DOI:10.1007/BF00904751.
- ^ Electronic structures of trifluoro-, tricyano-, and trinitromethane and their conjugate bases, in Journal of the American Chemical Society, vol. 113, n. 13, 1991, pp. 4751–4755, DOI:10.1021/ja00013a007.
