Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Trinitromethane: Difference between pages - Misplaced Pages

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Difference between pages)
Page 1
Page 2
Content deleted Content addedVisualWikitext
Revision as of 14:18, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 402701509 of page Trinitromethane for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 14:23, 29 December 2024 edit Trasheater Midir (talk | contribs)Extended confirmed users3,648 edits →ReferencesTag: ProveIt edit 
Line 1: Line 1:
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 402699502 | verifiedrevid = 470616111
| ImageFile = trinitromethane.svg | ImageFile = trinitromethane.svg
| ImageFile1 = Trinitromethane-3D-vdW.png
| ImageSize = | ImageSize =
| Name = Trinitromethane | Name = Trinitromethane
| Reference =<ref>{{Merck12th|id=9859}}.</ref> | Reference = <ref>{{Merck12th|id=9859}}.</ref>
| IUPACName = Trinitromethane | IUPACName = Trinitromethane
| OtherNames = Nitroform | OtherNames = Nitroform
| SystematicName =
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| index1_label = anion
| InChI = 1/CHN3O6/c5-2(6)1(3(7)8)4(9)10/h1H | InChI = 1/CHN3O6/c5-2(6)1(3(7)8)4(9)10/h1H
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/CHN3O6/c5-2(6)1(3(7)8)4(9)10/h1H | StdInChI = 1S/CHN3O6/c5-2(6)1(3(7)8)4(9)10/h1H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LZGVDNRJCGPNDS-UHFFFAOYSA-N | StdInChIKey = LZGVDNRJCGPNDS-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 517-25-9 --> | CASNo = 517-25-9
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | EC-number = 208-236-8
| UNII = Q5IR4EM1R0
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | EC_number = 208-236-8
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10157 | ChemSpiderID = 10157
| PubChem = | PubChem = 10602
| PubChem1 = 11355947
| SMILES = C((=O))((=O))(=O) | SMILES = C((=O))((=O))(=O)
| InChI1=1S/CN3O6/c5-2(6)1(3(7)8)4(9)10/q-1
| InChIKey1 = LVFFNJCUYJXEAZ-UHFFFAOYSA-N
| SMILES1 = C(=())((=O))(=O)
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = CHN<sub>3</sub>O<sub>6</sub> | Formula = CHN<sub>3</sub>O<sub>6</sub>
| MolarMass = 151.04 g/mol | MolarMass = 151.04 g/mol
| Density = 1.469 g/cm<sup>3</sup> | Density = 1.469 g/cm<sup>3</sup>
| Appearance = Pale yellow crystals | Appearance = Pale yellow crystals
| MeltingPtC = 15 | MeltingPtC = 15
| BoilingPt = | BoilingPt =
| Solubility = 44g/100ml at 20°C | Solubility = 44g/100ml at 20 °C
| pKa = 0.25 (see text) | pKa = 0.25 (see text)
}} }}
| Section3 =
| Section4 =
| Section5 =
| Section6 =
| Section7 = {{Chembox Hazards | Section7 = {{Chembox Hazards
| MainHazards = Oxidant, Explosive (esp. in contact with metals), Corrosive. | MainHazards = Oxidant, Explosive (esp. in contact with metals), Corrosive.
| NFPA-H = 3 | NFPA-H = 3
| NFPA-F = 1 | NFPA-F = 1
| NFPA-R = 4 | NFPA-R = 4
| NFPA-O = OX | NFPA-S = OX
}}| Section8 = {{Chembox Related }}
| Section8 = {{Chembox Related
| OtherCpds = ]<br/>]<br/> ] | OtherCompounds = ]<br/>]<br/> ]
}} }}
}} }}

'''Trinitromethane''', also referred to as '''nitroform''', is a ] and ] with chemical formula HC(NO<sub>2</sub>)<sub>3</sub>. It was first obtained in 1857 as the ammonium salt by the Russian chemist {{Ill|Leon Shishkov|lt=Leon Nikolaevich Shishkov|ru|Шишков, Леон Николаевич}} (1830–1908).<ref>For biographical information about Leon Nikolaevich Shishkov, see </ref><ref>See:
* {{cite journal |last1=Chichkoff |first1=Léon |title=Note sur le nitroforme |journal=Comptes rendus |date=1857 |volume=45 |pages=144–146 |url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015035405979&view=1up&seq=154 |trans-title=Note on nitroform |language=French}}
* {{cite journal |last1=Schischkoff |first1=L. |title=Ueber das Nitroform |journal=Annalen der Chemie |date=1857 |volume=103 |issue=3 |pages=364–366 |url=https://babel.hathitrust.org/cgi/pt?id=uva.x002457949&view=1up&seq=378 |trans-title=On nitroform |language=German|doi=10.1002/jlac.18571030316 |s2cid=97319556 }}
* Abstracted in: {{cite journal |last1=Schischkoff |first1=L. |title=On nitroform |journal=The Chemical Gazette |date=1857 |volume=15 |page=448 |url=https://books.google.com/books?id=xQcAAAAAMAAJ&pg=PA448}}
* Abstracted in: {{cite journal |last1=Schischkoff |first1=L. |title=On nitroform |journal=Philosophical Magazine |date=1858 |volume=15 |page=302 |url=https://books.google.com/books?id=1bZJAQAAMAAJ&pg=PA302 |series=4th series}}</ref> In 1900, it was discovered that nitroform can be produced by the reaction of ] with anhydrous ].<ref>The Italian chemist Adolfo Baschieri discovered that nitroform (Italian: ''nitroformio'') could be produced from acetylene (''acetilene'') and nitric acid (''acido nitrico'').
* {{cite journal |last1=Baschieri |first1=A. |title=Sul comportamento dell' acetilene con alcuni ossidanti |journal=Atti della Reale Accademia dei Lincei |date=1900 |volume=9 (part I) |pages=391–393 |url=https://www.biodiversitylibrary.org/item/155899#page/397/mode/1up |series=5th series |trans-title=On the behavior of acetylene with some oxidizers |language=Italian}} See p. 392.
* Abstracted in German in: {{cite journal |last1=Baschieri |first1=A. |title=Über das Verhalten des Acetylens gegen einige Oxydationsmittel |journal=Chemisches Zentralblatt |date=1900 |volume=4 (part II) |page=528 |url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015020184084&view=1up&seq=576 |series=5th series |trans-title=On the behavior of acetylene towards some oxidizers |language=German}}
* See also: {{cite book |last1=Nieuwland |first1=Julius A. |last2=Vogt |first2=Richard R. |title=The Chemistry of Acetylene |date=1945 |publisher=Reinhold Publishing Corp. |location=New York City, New York, USA |page= |url=https://archive.org/details/in.ernet.dli.2015.239313}}</ref> 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 ] under mild basic conditions.<ref>{{ cite journal | first1 = A. A. | last1 = Gakh | first2 = J. C. | last2 = Bryan | first3 = M. N. | last3 = Burnett | first4 = P. V. | last4 = Bonnesen | title = Synthesis and structural analysis of some trinitromethanide salts | journal = Journal of Molecular Structure | year = 2000 | volume = 520 | issue = 1–3 | pages = 221–228 | doi = 10.1016/S0022-2860(99)00333-6 | bibcode = 2000JMoSt.520..221G | url = https://zenodo.org/record/1259627 }}</ref>

==Acidity==
Trinitromethane as a neutral molecule is colorless. It is highly acidic, easily forming an intensely yellow anion, (NO<sub>2</sub>)<sub>3</sub>C<sup>−</sup>. The ] of trinitromethane has been measured at 0.17 ± 0.02 at 20 °C, which is remarkably acidic for a methane derivative.<ref>{{ cite journal | first1 = S. S. | last1 = Novikov | first2 = V. I. | last2 = Slovetskii | first3 = S. A. | last3 = Shevelev | first4 = A. A. | last4 = Fainzilberg | title = Spectrophotometric Determination of the Dissociation Constants of Aliphatic Nitro Compounds | journal = Russian Chemical Bulletin | year = 1962 | volume = 11 | issue = 4 | pages = 552–559 | doi = 10.1007/BF00904751 }}</ref> Trinitromethane easily dissolves in water to form an acidic yellow solution.

There is some evidence that the anion, which obeys the 4''n''+2 ], displays Y-aromaticity, a form of ] disputed among chemists.<ref>{{ cite journal | title = Electronic structures of trifluoro-, tricyano-, and trinitromethane and their conjugate bases | first1 = J. | last1 = Cioslowski | first2 = S. T. | last2 = Mixon | first3 = E. D. | last3 = Fleischmann | journal = Journal of the American Chemical Society | year = 1991 | volume = 113 | issue = 13 | pages = 4751–4755 | doi = 10.1021/ja00013a007 }}</ref>

==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(NO<sub>2</sub>)<sub>3</sub> is a lemon yellow crystalline solid that decomposes slowly at room temperatures and explodes above 95&nbsp;°C. The ammonium salt is somewhat more stable, and deflagrates or explodes above 200&nbsp;°C. The hydrazine salt, ] is thermally stable to above 125&nbsp;°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 ], trinitromethane reacts with ], giving ].<ref>{{Cite book |url=https://books.google.com/books?id=JL0rilW6mMEC&q=Hurd+Starke |title=British Abstracts: Series A. |date=1951 |language=en}}</ref> This compound is a solvent to ] and a precursor to high explosives such as ] and ].

==References==
{{reflist|colwidth=30em}}

== Further reading ==
*{{Cite encyclopedia |title=Nitromethanes |encyclopedia=Encyclopedia of Oxidizers |publisher=De Gruyter |last=Schmidt |first=Eckart W. |date=2022 |pages=2820–2832 |doi=10.1515/9783110750294-022 |isbn=978-3-11-075029-4|chapter=Trinitromethane}}

]
]
]