Angeli's salt

Angeli's salt
Identifiers
CAS Number	13826-64-7 ;
3D model (JSmol)	Interactive image;
PubChem CID	10129945;
UNII	S8LUE47R4Z ;
	InChI InChI=1S/N2O3.2Na/c3-1-2(4)5;;/q;2*+1 Key: XDPWLJKQGUTUKZ-UHFFFAOYSA-N;
	SMILES N(=O)[N+](=O)[O-].[Na+].[Na+];
Properties
Chemical formula	N2Na2O3
Molar mass	121.991 g·mol−1
Appearance	white solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Angeli's salt, sodium trioxodinitrate, is the inorganic compound with the formula Na₂[N₂O₃]. It contains nitrogen in an unusual reduced state. It is a colorless, water-soluble solid, a salt. In research, this salt is used as a source of the metastable nitroxyl (HNO), which is a signalling molecule in nature.[1] It is also known by the name sodium trioxodinitrate(II) monohydrate.

As first reported by Angelo Angeli in 1896, the salt is prepared by combining hydroxylamine and an organic nitrate, as a source of NO₂⁺:[2][3]

NH₂OH + RONO₂ + 2 NaOR' → ROH + 2 R'OH + Na₂N₂O₃

The structure of the hydrate has been confirmed by X-ray crystallography. The anion is planar. Starting from the ONN end, the bond distances are 1.35 (N-O), 1.26 (N-N), 1.31 (N-O), 1.32 Å (N-O). Negative charge is on the oxygen atoms at opposite ends of the molecule. The angles are single oxygen to nitrogen-nitrogen bond 112.9°, nitrogen-nitrogen bond to trans oxygen 118.4°, nitrogen-nitrogen bond to cis oxygen 122.5°. This means that the nitrogen-nitrogen bond is a double bond, and that the cis oxygen is slightly repelled by the single oxygen.[4]

Reaction of Angeli's salt with secondary amines in the presence of a proton source results in extrusion of N₂ via isodiazenes as proposed intermediates.[5]

References

Nakagawa, H. (2013). "Controlled release of HNO from chemical donors for biological applications". J. Inorg. Biochem. 118: 187–190. doi:10.1016/j.jinorgbio.2012.10.004. PMID 23140899.
A. Angeli (1896). "Sopra la nitroidrossilammina". Gazz. Chim. Ital. 26: 17–28.
Hughes, Martin N.; Cammack, Richard (1999). "Synthesis, chemistry, and Applications of Nitroxyl Ion Releasers Sodium Trioxodinitrate or Angeli's Salt and Piloty's Acid". Methods in Enzymology (Nitric Oxide, Part C: Biological and Antioxidant Activities). 301: 279–287. doi:10.1016/S0076-6879(99)01092-7. PMID 9919577.
Hope, Hakon; Sequeira, Michael R. (February 1973). "Angeli's salt. Crystal structure of sodium trioxodinitrate(II) monohydrate, Na₂N₂O₃^.H₂O". Inorganic Chemistry. 12 (2): 286–288. doi:10.1021/ic50120a008.
1937-, Carey, Francis A. (2007). Advanced organic chemistry. Part B, Reactions and synthesis. Sundberg, Richard J., 1938- (5th ed.). New York, NY: Springer. ISBN 9781601195494. OCLC 223941000.CS1 maint: numeric names: authors list (link)

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[1] Nakagawa, H. (2013). "Controlled release of HNO from chemical donors for biological applications". J. Inorg. Biochem. 118: 187–190. doi:10.1016/j.jinorgbio.2012.10.004. PMID 23140899.

[2] A. Angeli (1896). "Sopra la nitroidrossilammina". Gazz. Chim. Ital. 26: 17–28.

[3] Hughes, Martin N.; Cammack, Richard (1999). "Synthesis, chemistry, and Applications of Nitroxyl Ion Releasers Sodium Trioxodinitrate or Angeli's Salt and Piloty's Acid". Methods in Enzymology (Nitric Oxide, Part C: Biological and Antioxidant Activities). 301: 279–287. doi:10.1016/S0076-6879(99)01092-7. PMID 9919577.

[4] Hope, Hakon; Sequeira, Michael R. (February 1973). "Angeli's salt. Crystal structure of sodium trioxodinitrate(II) monohydrate, Na₂N₂O₃^.H₂O". Inorganic Chemistry. 12 (2): 286–288. doi:10.1021/ic50120a008.

[5] 1937-, Carey, Francis A. (2007). Advanced organic chemistry. Part B, Reactions and synthesis. Sundberg, Richard J., 1938- (5th ed.). New York, NY: Springer. ISBN 9781601195494. OCLC 223941000.CS1 maint: numeric names: authors list (link)