2-(Dicyanomethylene)croconate

2-(Dicyanomethylene)croconate
	Skeletal formula of 2-(dicyanomethylene)croconate
Names
	IUPAC name 2-(Dicyanomethylene)croconate[citation needed]
Identifiers
ChemSpider	26234929
Jmol 3D model	Interactive image; Interactive image; Interactive image
	InChI InChI=1S/C8N2O4/c9-1-3(2-10)4-5(11)7(13)8(14)6(4)12/q-2 Key: COPWPGZONJUOON-UHFFFAOYSA-N ; 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 [O-]c1c(:o)c(:o)c([O-])c1:c(C#N)C#N ; [O-][C]1C(=O)C(=O)[C]([O-])C1=C(C#N)C#N ; C(#N)C(=C1C(=O)C(=C(C1=O)[O-])[O-])C#N ;
Properties
Chemical formula	C; 8N; 2O; 4
Molar mass	188.0966 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

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