Furantetracarboxylic acid

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Furantetracarboxylic acid
Furantetracarboxylic acid.svg
Names
Preferred IUPAC name
Furantetracarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
  • 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

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.

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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