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Concept
Oxalate
Summary
Oxalate (IUPAC: ethanedioate) is an anion with the formula C2O42−. This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate (Na2C2O4), and several esters such as dimethyl oxalate (C2O4(CH3)2). It is a conjugate base of oxalic acid. At neutral pH in aqueous solution, oxalic acid converts completely to oxalate.
The dissociation of protons from oxalic acid proceeds in a stepwise manner; as for other polyprotic acids, loss of a single proton results in the monovalent hydrogenoxalate anion HC2O4−. A salt with this anion is sometimes called an acid oxalate, monobasic oxalate, or hydrogen oxalate. The equilibrium constant (Ka) for loss of the first proton is 5.37e-2 (pKa = 1.27). The loss of the second proton, which yields the oxalate ion, has an equilibrium constant of 5.25e-5 (pKa = 4.28). These values imply, in solutions with neutral pH, no oxalic acid and only trace amounts of hydrogen oxalate exist. The literature is often unclear on the distinction between H2C2O4, HC2O4−, and C2O42−, and the collection of species is referred to as oxalic acid.
The oxalate anion exists in a nonplanar conformation where the O–C–C–O dihedrals approach 90° with approximate D2d symmetry. When chelated to cations, oxalate adopts the planar, D2h conformation. However, in the structure of Cs2C2O4 the O–C–C–O dihedral angle is 81(1)°. Therefore, Cs2C2O4 is more closely approximated by a D2d symmetry structure because the two CO2 planes are staggered. Two structural forms of Rb2C2O4 have been identified by single-crystal X-ray diffraction: one contains a planar and the other a staggered oxalate.
The barrier to rotation about this bond is calculated to be roughly 2–6 kcal/mol for the free dianion, C2O42−. Such results are consistent with the interpretation that the central carbon–carbon bond is regarded as a single bond with minimal π interactions between the two CO2− units.
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