Furantetracarboxylic acid

In chemistry, furantetracarboxylic acid is an organic compound with formula C
8H
4O
9, or (C4O)(-(CO)OH)4, which can be viewed as deriving from furan C
4H
4O through replacement of the four hydrogen atoms by carboxyl functional groups -(CO)OH.

Furantetracarboxylic acid
Names
Preferred IUPAC name
Furantetracarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C8H4O9/c9-5(10)1-2(6(11)12)4(8(15)16)17-3(1)7(13)14/h(H,9,10)(H,11,12)(H,13,14)(H,15,16)
    Key: IREPGQRTQFRMQR-UHFFFAOYSA-N
  • C1(=C(OC(=C1C(=O)O)C(=O)O)C(=O)O)C(=O)O
Properties
C8H4O9
Molar mass 244.11 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

By removal of four protons, the acid is expected to yield the anion C
8O4−
9, furantetracarboxylate, which is one of the oxocarbon anions (consisting solely of oxygen and carbon. By loss of 1 through 3 protons it forms the anions C
8H
3O−
9, C
8H
2O2−
9, and C
8HO3−
9, called respectively trihydrogen-, dihydrogen-, and hydrogenfurantetracarboxylate. The same names are used for the corresponding esters.

The acid can be obtained by from dioxalylsuccinate.[1][2][3]

The salt rubidium trihydrogenfurantetracarboxylate RbH
3C
8O
9 crystallizes as white needles.[4]

See also

References
  1. B. I. Zapadinskii, B. I. Liogon'kii, and A. A. Berlin (1973), Syntheses of Tetracarboxylic Acids. Russian Chemical Reviews, volume 42 issue 11, page 939. Online version accessed on 2010-01-03.
  2. H.Sutter (1932), Annalen, volume 499, page 47. Cited by Zapadinskii et al.
  3. T.Reichstein, A.Grussner, K.Schiudlerk, and E. Hardmeyer (1933), Helv.Chim.Acta, volume 16, page 276. Cited by Zapadinskii et al.
  4. Iain C. Paul and Leslie L. Martin (1967), The crystal and molecular structure of the monorubidium salt of furantetracarboxylic acid. Acta Crystallogr. volume 22 pages 559-567 doi:10.1107/S0365110X67001136
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