- Source: 1,3-Bis(dicyanomethylene)squarate
1,3-Bis(dicyanomethylene)squarate is a divalent anion with chemical formula C10N4O2−2 or ((N≡C−)2C=)2(C4O2)2−. It is one of the pseudo-oxocarbon anions, as it can be described as a derivative of the squarate oxocarbon anion C4O2−4 through the replacement of two opposite oxygen atoms by dicyanomethylene groups =C(−C≡N)2.
The anion can be obtained by reacting squaric acid with aniline to form the diester 1,3-dianiline squarate (a yellow solid), before treating the diester with malononitrile (N≡C−)2CH2 and sodium ethoxide to give the disodium tetrahydrate salt 2Na+·C10N4O2−2·4H2O, an orange water-soluble solid. The hydrated salt loses the water below 100 °C, but the resulting anhydrous salt is stable up to 400 °C. Reaction of the sodium salt with salts of other cations in ethanol affords the following salts:
dipotassium sodium chloride 2K+·Na+·Cl−·K2C10N4O2−2·1⁄2CH3CN, orange
rubidium sodium chloride 7Rb+·Na+·2Cl−·3Rb2C10N4O2−2·CH3CH2OH, orange, loses 1 ethanol at 96 °C, stable to 361 °C
magnesium disodium nitrate, Mg2+·2Na+C10N4O2−2·NO−3·6H2O·CH3CH2OH, orange, loses 1 ethanol and 6 H2O at 78 °C, stable to 482 °C
calcium, Ca2+·C10N4O2−2·6H2O, purple, dehydrates at 63–102 °C, stable to 468 °C
barium, Ba2+·C10N4O2−2·4H2O, orange, dehydrates at 71–96 °C, stable to 457 °C
tetra-n-butylammonium sodium, 2(C4H9)4N+·2Na+·2Cl−·2C10N4O2−2·CH3CH2OH, orange, loses 1 ethanol and 2 tetrabutylammonium at 111 °C, stable to 238 °C
Nuclear magnetic resonance shows that the aromatic character of the squarate core is retained.
See also
Croconate violet
Croconate blue
1,2-Bis(dicyanomethylene)squarate
References
Kata Kunci Pencarian:
- 1,3-Bis(dicyanomethylene)squarate
- 1,2-Bis(dicyanomethylene)squarate
- Squaric acid
- Croconate violet
- 2-(Dicyanomethylene)croconate
- Croconate blue
- Pseudo-oxocarbon anion
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