2-(Dicyanomethylene)croconate

2-(Dicyanomethylene)croconate
	2-(dicyanomethylene)croconate dianion
Names
	Preferred IUPAC name 4-(Dicyanomethylene)-3,5-dioxo-1-cyclopentene-1,2-diolate
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	26234929 ;
PubChem CID	139033599;
CompTox Dashboard (EPA)	DTXSID701029307 ;
	InChI InChI=1S/C8H2N2O4/c9-1-3(2-10)4-5(11)7(13)8(14)6(4)12/h13-14H/p-2 Key: UOFODKSWJURJDQ-UHFFFAOYSA-L ;
	SMILES C(#N)C(=C1C(=O)C(=C(C1=O)[O-])[O-])C#N;
Properties
Chemical formula	C8N2O42−
Molar mass	188.099 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-(Dicyanomethylene)croconate is a divalent anion with chemical formula C
₈N
₂O²⁻
₄ or ((N≡C−)₂C=)(C₅O₄)²⁻. It is one of the pseudo-oxocarbon anions, as it can be described as a derivative of the croconate oxocarbon anion C
₅O²⁻
₅ through the replacement of one oxygen atom by a dicyanomethylene group =C(−C≡N)₂.

The anion was synthesized and characterized by A. Fatiadi in 1980, by hydrolysis of croconate violet treated with potassium hydroxide.^[1] It gives an orange solution in water.

References

^ Alexander J. Fatiadi (1980), "Pseudooxocarbons. Synthesis of 1,2,3-tris(dicyanomethylene)croconate salts. A new bond-delocalized dianion, croconate blue". Journal of Organic Chemistry volume 45, pages 1338–1339. doi:10.1021/jo01295a044

[fati2-1] Alexander J. Fatiadi (1980), "Pseudooxocarbons. Synthesis of 1,2,3-tris(dicyanomethylene)croconate salts. A new bond-delocalized dianion, croconate blue". Journal of Organic Chemistry volume 45, pages 1338–1339. doi:10.1021/jo01295a044

[1]

See also

References