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- Q4545671 subject Q8856198.
- Q4545671 abstract "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−·K2C10N4O2−2·0.5CH3CN, 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(C4H5)4N+·2Na+·2Cl−·2C10N4O2−2·CH3CH2OH, orange, loses 1 ethanol and 2 TBA at 111 °C, stable to 238 °CNuclear magnetic resonance shows that the aromatic character of the squarate core is retained.".
- Q4545671 thumbnail Chemfm_1_3_bis_dicyanomethylene_squarate_2neg.svg?width=300.
- Q4545671 wikiPageWikiLink Q101487.
- Q4545671 wikiPageWikiLink Q1112.
- Q4545671 wikiPageWikiLink Q170409.
- Q4545671 wikiPageWikiLink Q171407.
- Q4545671 wikiPageWikiLink Q186414.
- Q4545671 wikiPageWikiLink Q209402.
- Q4545671 wikiPageWikiLink Q36496.
- Q4545671 wikiPageWikiLink Q412779.
- Q4545671 wikiPageWikiLink Q419572.
- Q4545671 wikiPageWikiLink Q4545650.
- Q4545671 wikiPageWikiLink Q462174.
- Q4545671 wikiPageWikiLink Q5187421.
- Q4545671 wikiPageWikiLink Q5187422.
- Q4545671 wikiPageWikiLink Q629.
- Q4545671 wikiPageWikiLink Q660.
- Q4545671 wikiPageWikiLink Q703.
- Q4545671 wikiPageWikiLink Q706.
- Q4545671 wikiPageWikiLink Q7115726.
- Q4545671 wikiPageWikiLink Q7254440.
- Q4545671 wikiPageWikiLink Q83147.
- Q4545671 wikiPageWikiLink Q8856198.
- Q4545671 wikiPageWikiLink Q895.
- Q4545671 wikiPageWikiLink Q903298.
- Q4545671 comment "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.".
- Q4545671 label "1,3-Bis(dicyanomethylene)squarate".
- Q4545671 depiction Chemfm_1_3_bis_dicyanomethylene_squarate_2neg.svg.