Oxalic acid
Oxalate, the conjugate base of oxalic acid, is an excellent ligand for metal ions. It usually binds as a bidentate ligand forming a 5-membered MC2O2 ring. An illustrative complex is potassium ferrioxalate, K3[Fe(C2O4)3]. The drug oxaliplatin exhibits improved water solubility relative to older platinum-based drugs, avoiding the dose-limiting side-effect of nephrotoxicity. Oxalic acid and oxalates can be oxidized by permanganate in an autocatalytic reaction. One of the main applications of oxalic acid is rust-removal, which arises because oxalate forms water-soluble derivatives with the ferric ion.