Methanetetracarboxylate

In chemistry, methanetetracarboxylate is a tetravalent anion with formula C
5
O4−
8
or C(COO)4. It has four carboxylate groups attached to a central carbon atom; so it has the same carbon backbone as neopentane. It is an oxocarbon anion, that is, consists only of carbon and oxygen.

Methanetetracarboxylate
Chemfm methanetetracarboxylate 4neg.svg
Dots that are highlighted in blue carry a partial negative charge.
Names
IUPAC name
methanetetracarboxylate[PubChem 1]
Identifiers
3D model (JSmol)
Properties
C5O8−4
Molar mass 188.049 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 term is also used for any salt with that anion; or for any ester with the C(COO)4 moiety.[1]

The salts and esters are relatively uncommon, and their uses appear to be limited to chemical research. The sodium salt Na4C(COO)4 can be obtained by oxidation of pentaerythritol C(CH2OH)4 with oxygen in sodium hydroxide solution at pH 10 and about 60 °C, in the presence of palladium as a catalyst.[2] The tetraethyl ester C(COO-C2H5)4 is traded as a specialty chemical and has been used in organic synthesis.[3]

The anion can be seen as the result of removing four protons from methanetetracarboxylic acid, a hypothetical organic compound with formula C5H4O8 or C(COOH)4. However this acid has not been synthesised (as of 2009), and is believed to be unstable.

ReferencesEdit

  1. ^ Backer, H. J.; Lolkema, J. (1939), Methanetetracarboxylic esters. Recueil des Travaux Chimiques des Pays-Bas et de la Belgique, volume 58, pages 23–33.
  2. ^ Japanese Patent 52128317, Sodium methanetetracarboxylate from pentaerythritol
  3. ^ Armin de Meijere, Rafael R. Kostikov, Andrei I. Savchenko, Sergei I. Kozhushkov (2004), Diethyl Cyclopropylidenemalonate: Facile Preparation, Generation in situ, and Various Transformations. European Journal of Organic Chemistry, volume 2004 issue 19, Pages 3992–4002.
  1. ^ "NKVMCSDLYHGDMD-UHFFFAOYSA-J". pubchem.ncbi.nlm.nih.gov. Retrieved 14 March 2019. IUPAC Name methanetetracarboxylate
  2. ^ "NKVMCSDLYHGDMD-UHFFFAOYSA-J". pubchem.ncbi.nlm.nih.gov. Retrieved 14 March 2019. PubChem CID: 57459306
  3. ^ "SID 137126464 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 14 March 2019. PubChem CID: 57459306
  4. ^ "NKVMCSDLYHGDMD-UHFFFAOYSA-J" (table). pubchem.ncbi.nlm.nih.gov. Retrieved 14 March 2019. Source External ID PubChem SID chemicalize.org by ChemAxon 280211 137126464
  5. ^ "SID 137126464 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 14 March 2019. PubChem SID: 137126464
  6. ^ "NKVMCSDLYHGDMD-UHFFFAOYSA-J". pubchem.ncbi.nlm.nih.gov. Retrieved 14 March 2019. Canonical SMILES C(=O)(C(C(=O)[O-])(C(=O)[O-])C(=O)[O-])[O-]
  7. ^ "NKVMCSDLYHGDMD-UHFFFAOYSA-J". pubchem.ncbi.nlm.nih.gov. Retrieved 14 March 2019. InChI InChI=1S/C5H4O8/c6-1(7)5(2(8)9,3(10)11)4(12)13/h(H,6,7)(H,8,9)(H,10,11)(H,12,13)/p-4
  8. ^ "NKVMCSDLYHGDMD-UHFFFAOYSA-J". pubchem.ncbi.nlm.nih.gov. Retrieved 14 March 2019. InChI Key NKVMCSDLYHGDMD-UHFFFAOYSA-J