2-(Dicyanomethylene)croconate

2-(Dicyanomethylene)croconate

Names
IUPAC name 2-(Dicyanomethylene)croconate
Identifiers
3D model (Jmol)	Interactive image Interactive image Interactive image
ChemSpider	26234929
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.

See also

• Croconate violet, 1,3-bis(dicyanomethylene)croconate
• Croconate blue, 1,2,3-tris(dicyanomethylene)croconate
• 1,2-Bis(dicyanomethylene)squarate
• 1,3-Bis(dicyanomethylene)squarate

References

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