Concept

Croconic acid

Summary
Croconic acid (also known as 4,5-dihydroxycyclopentenetrione, crocic acid or pentagonic acid) is a chemical compound with formula or . It has a cyclopentene backbone with two hydroxyl groups adjacent to the double bond and three ketone groups on the remaining carbon atoms. It is sensitive to light, soluble in water and ethanol and forms yellow crystals that decompose at 212 °C. The compound is acidic and loses the protons from the hydroxyl groups (pKa1 = 0.80 and pKa2 = 2.24 at 25 °C). The resulting anions, hydrogencroconate and croconate are also quite stable. The croconate ion, in particular, is aromatic and symmetric, as the double bond and the negative charges become delocalized over the five CO units (with two electrons, Hückel's rule means this is an aromatic configuration). The lithium, sodium and potassium croconates crystallize from water as dihydrates but the orange potassium salt can be dehydrated to form a m
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