2-(Dicyanomethylene)croconate

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.

2-(Dicyanomethylene)croconate
Names
Preferred IUPAC name
4-(Dicyanomethylene)-3,5-dioxo-1-cyclopentene-1,2-diolate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C8H2N2O4/c9-1-3(2-10)4-5(11)7(13)8(14)6(4)12/h13-14H/p-2 Y
    Key: UOFODKSWJURJDQ-UHFFFAOYSA-L Y
  • C(#N)C(=C1C(=O)C(=C(C1=O)[O-])[O-])C#N
Properties
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

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
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