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{{chembox
| verifiedrevid =
| Name = Sodium hyponitrite (trans isomer)
| ImageFile = Sodium_hyponitrite.png
| ImageName =
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| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 60884-94-8 (hydrate)
| CASNo_Ref =
| PubChem = 10034601, 24869787
| ChemSpiderID = 8210166
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| InChIKey = HLJWMCUZPYEUDI-UHFFFAOYSA-L
| SMILES = N(=N[O-])[O-].[Na+].[Na+]
| SMILES1 = [Na+].[O-]/N=N/[O-].[Na+]
| SMILES1_Comment = ''trans''-form
| SMILES2 = [Na+].[O-]\N=N/[O-].[Na+]
| SMILES2_Comment = ''cis''-form
}}
|Section2={{Chembox Properties
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| Odor =
| Density = 2.466 g/cm<sup>3</sup>
| MeltingPtC =
| BoilingPtC =
| BoilingPt_notes = decomposes
| Solubility = soluble
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|Section7={{Chembox Hazards
| ExternalSDS =
|
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| GHS_ref =
| NFPA-H =
| NFPA-F =
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}}
'''Sodium hyponitrite''' is a solid [[ionic compound]] with formula {{chem|Na|2|N|2|O|2}} or ({{chem|Na|+}})<sub>2</sub>[ON=NO]<sup>2−</sup>.<ref name = "Wiberg&Holleman">Egon Wiberg, Arnold Frederick Holleman (2001) ''Inorganic Chemistry'', Elsevier {{ISBN|0-12-352651-5}}</ref>
There are ''cis'' and ''trans'' forms of the [[hyponitrite]] ion {{chem|N|2|O|2|2-}}. The ''trans'' form is more common, but the ''cis'' form can be obtained too, and it is more reactive than the ''trans'' form.<ref name = "Wiberg&Holleman"/><ref name="feld"/>
==Preparation==▼
==''Trans'' isomer==
The ''trans'' isomer is colorless and soluble in water and insoluble in [[ethanol]] and [[diethyl ether|ether]].<ref name="tram">Trambaklal Mohanlal Oza, Rajnikant Hariprasad Thaker (1955), "The Thermal Decomposition of Silver Hyponitrite". Journal of the American Chemical society, volume 77, issue 19, pages 4976–4980. {{doi|10.1021/ja01624a007}}</ref><ref name="scott"/>
▲===Preparation===
Sodium hyponitrite (''trans'') is conventionally prepared by [[reduction (chemistry)|reduction]] of [[sodium nitrite]] with [[sodium amalgam]].<ref>{{cite journal |author1=Addison, C. C. |author2=Gamlen G. A. |author3=Thompson, R. | journal = [[J. Chem. Soc.]] | year = 1952 | pages = 338–345 | doi = 10.1039/jr9520000338 | title = 70. The ultra-violet absorption spectra of sodium hyponitrite and sodium α-oxyhyponitrite : the analysis of mixtures with sodium nitrite and nitrate}}</ref><ref>{{cite journal | author = Neumann, R. C., Jr. Bussey, R. J. | journal = [[J. Am. Chem. Soc.]] | year = 1970 | volume = 92 | pages = 2440–2445 | doi = 10.1021/ja00711a039 | title = High pressure studies. V. Activation volumes for combination and diffusion of geminate tert-butoxy radicals | issue = 8}}</ref><ref>{{Greenwood&Earnshaw}}</ref>
:2 NaNO<sub>2</sub> + 4 Na(Hg) + 2 H<sub>2</sub>O → Na<sub>2</sub>N<sub>2</sub>O<sub>2</sub> + 4 NaOH + 4 Hg
Sodium hyponitrite (''trans'') was prepared in 1927 by [[A. W. Scott]] by reacting [[alkyl]] [[nitrites]], [[hydroxylammonium chloride]], and [[sodium ethoxide]]<ref name="scott">A. W. Scott (1927), "Sodium Hyponitrite". [[J. Am. Chem. Soc.]], volume = 49, issue 4, pages = 986–987. {{doi|10.1021/ja01403a502}}</ref><ref name="InorgChem">{{cite book | title = Inorganic Chemistry | edition = 3rd | chapter = Chapter 15: The group 15 elements | author1 = Catherine E. Housecroft | author2 = Alan G. Sharpe| publisher = Pearson | year = 2008 | isbn = 978-0-13-175553-6 | page = 468}}</ref>
: RONO + NH<sub>2</sub>OH + 2 EtONa → Na<sub>2</sub>N<sub>2</sub>O<sub>2</sub> + ROH + 2 EtOH
An earlier method, published by [[David Mendenhall|D. Mendenhall]] in 1974, reacted gaseous [[nitric oxide]] ({{chem|N|O}}) with [[sodium]] metal in [[1,2-dimethoxyethane]], [[toluene]], and [[benzophenone]]. The salt was then extracted with water.<ref name="mend">G. David Mendenhall (1974), "Convenient synthesis of silver hyponitrite". Journal of the American Chemical society, volume 96, issue 15, page 5000. {{doi|10.1021/ja00822a054}}</ref> The method was later modified to use [[pyridine]]{{Citation needed|date=April 2010}}.
Other methods included [[oxidation]] of a concentrated solution of [[hydroxylamine]] with sodium nitrite in an alkaline medium{{Citation needed|date=February 2017}}; or [[electrolysis]] of sodium nitrite.<ref>Polydoropoulos, C. N. Chem. Ind. (London) 1963, 1686 and references therein.</ref>
===Hydrates===
A variety of [[hydrates]] {{chem|Na|2|N|2|O|2}}({{chem|H|2|O}})<sub>''x''</sub> of the ''trans'' isomer have been reported, with ''x'' including 2, 3.5, 4, 5, 6, 7, 8, and 9;<ref name="partin">James Riddick Partington and Chandulal Chhotalal Shah (1931), "Investigations on hyponitrites. Part I. Sodium hyponitrite: preparation and properties". Journal of the Chemical Society (Resumed), paper CCLXXXII, pages 2071-2080. {{doi|10.1039/JR9310002071}}</ref><ref name="tram"/><ref name="polyhydr">C.N. Polydoropoulos, S.D. Voliotis (1967), "Sodium hyponitrite hexahydrate". Journal of Inorganic and Nuclear Chemistry, volume 29, issue 12, pages 2899–2901. {{doi|10.1016/0022-1902(67)80121-0}}</ref> but there is some dispute.<ref name="stucky">Gary L. Stucky, Jack L. Lambert, R. Dean Dragsdorf (1969), "The hydrates of sodium hyponitrite". Journal of Inorganic and Nuclear Chemistry, volume 31, issue 1, pages 29–32 {{doi|10.1016/0022-1902(69)80050-3}}</ref>
The hydration water seems to be just trapped in the crystal lattice rather than coordinated to the ions.<ref name="stucky"/> The anhydrous substance can be obtained by drying the hydrates over [[phosphorus pentoxide]] and then heating them to 120 °C.<ref name="stucky"/>
===Reactions===
Sodium hyponitrite (''trans'') in solution is decomposed by [[carbon dioxide]] {{chem|C|O|2}} from air to form [[sodium carbonate]].<ref name="conner">Charlotte N. Conner, Caroline E. Donald, Martin N. Hughes, Christina Sami (1989), "The molar absorptivity of sodium hyponitrite". Polyhedron, volume 8, issue 21, pages 2621-2622. {{doi|10.1016/S0277-5387(00)81166-3}}</ref>
Liquid [[dinitrogen tetroxide|N<sub>2</sub>O<sub>4</sub>]] oxidises sodium hyponitrite (''trans'') to give sodium [[peroxohyponitrite]] {{chem|Na|2|2+}}[ON=NOO]<sup>2−</sup>).<ref name="hughN2O4">M. N. Hughes and H. G. Nicklin (1969), "The action of dinitrogen tetroxide on sodium hyponitrite".
Journal of the Chemical Society D: Chemical Communications, volume 1969, issue 2, page 80a. {{doi|10.1039/C2969000080A}}</ref><ref name = "Wiberg&Holleman"/>
==''Cis'' isomer==
The ''cis'' isomer of sodium hyponitrite is a white crystalline solid, insoluble in [[aprotic]] solvents, and (unlike the ''trans'' isomer) decomposed by water and other [[protic]] solvents.<ref name="feld"/>
===Preparation===
The ''cis'' isomer of can be prepared by passing [[nitric oxide]] ({{chem|N|O}}) through a solution of [[sodium]] metal in liquid [[ammonia]] at −50 °C.<ref name = "Wiberg&Holleman"/>
The ''cis'' isomer was also obtained in 1996 by [[Claus Feldmann|C. Feldmann]] and [[martin Jansen|M. Jansen]] by heating [[sodium oxide]] {{chem|Na|2|O}} with 77 [[kilopascal|kPa]] of [[nitrous oxide]] {{chem|N|2|O}} (laughing gas) in a sealed tube at 360 °C for 2 hours. The two reagents combined to yield the ''cis'' hyponitrite quantitatively as white microcrystals.<ref name="InorgChem" /><ref name="feld">Claus Feldmann, Martin Jansen (1996), "''cis''-Sodium Hyponitrite - A New Preparative Route and a Crystal Structure Analysis". Angewandte Chemie International Edition in English, volume 35, issue 15, pages 1728–1730. {{doi|10.1002/anie.199617281}}</ref>
===Properties and reactions===
The anhydrous ''cis'' salt is stable up to 325 °C, when it disproportionates to [[nitrogen]] and [[sodium orthonitrite]]:<ref name="feld"/>
: 3 {{chem|Na|2|N|2|O|2}} → 2 {{chem|Na|3|O}}({{chem|N|O|2}}) + 2 {{chem|N|2}}
It is generally more reactive than the ''trans'' isomer.<ref name = "Wiberg&Holleman"/>
==See also==
* [[
==References==
{{Reflist}}
[[Category:Nitrites]]▼
{{Sodium compounds}}
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