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Hydrogenoxalate

Ion

Ion

Hydrogenoxalate or hydrogen oxalate (IUPAC name: 2-Hydroxy-2-oxoacetate) is an anion with chemical formula or , derived from oxalic acid by the loss of a single proton; or, alternatively, from the oxalate anion by addition of a proton. The name is also used for any salt containing this anion. Especially in older literature, hydrogenoxalates may also be referred to as bioxalates, acid oxalates, or monobasic oxalates. Hydrogenoxalate is amphoteric, in that it can react both as an acid or a base.

Well characterized salts include sodium hydrogenoxalate (), potassium hydrogenoxalate (), ammonium hydrogenoxalate (), rubidium hydrogenoxalate () and dimethylammonium hydrogenoxalate ().

Structure

Most hydrogenoxalate salts are hydrated. For example, potassium hydrogen oxalate crystallizes as . These materials exhibit extended structures resulting from extensive hydrogen bonding and anion-cation interactions. The hydrates dehydrate upon heating: : Proton transfer in hydrogen oxalates has been studied.

References

References

  1. "Hydrogen oxalate".
  2. (1 January 1992). "The role of coupling in intramolecular proton transfer reactions. The hydrogen oxalate anion as an example". Canadian Science Publishing.
  3. (1984). "Neutron diffraction study of sodium hydrogen oxalate monohydrate, NaHC2O4·H2O, at 120 K". Acta Crystallographica.
  4. (11 April 2015). "Crystal structure of dimethylammonium hydrogen oxalate hemi(oxalic acid)". International Union of Crystallography (IUCr).
  5. (2006). "The polymeric anhydrous rubidium hydrogen oxalate". Acta Crystallographica.
  6. (1971). "The crystal structures of normal and deuterated sodium hydrogen oxalate monohydrate NaHC2O4·H2O and NaDC2O4·D2O. Hydrogen bond studies XXXVI". The Journal of Chemical Physics.
  7. (1929). "The decomposition of potassium hydrogen oxalate hemihydrate". The Royal Society.
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