Deltic acid
Deltic acid or dihydroxycyclopropenone is a chemical substance with the chemical formula C3O(OH)2. It can be viewed as a ketone and double alcohol of cyclopropene. At room temperature, it is a stable white solid, soluble in diethyl ether, that decomposes (sometimes explosively) between 140 °C and 180 °C, and reacts slowly with water.
The synthesis of deltic acid was first described in 1975 by David Eggerding and Robert West.
Derivatives
Deltate and salts
Deltic acid is considered an acid because unlike most alcohols, the hydroxyl groups lose their protons (pK1 =2.57, pK2=6.03), leaving behind the symmetric deltate anion, C3O32−.
The first deltate salts (of lithium and potassium) were described in 1976, also by Eggerding and West. Lithium deltate Li2C3O3 is a water-soluble white solid. Like the other cyclic dianions with formula (CO)n2−, the deltate anion has a pronounced aromatic character which contributes to its relative stability.
Analogs
An analog of the deltate anion can be obtained by replacing the three oxygen atoms (=O or -O−) by cyanoimino groups (=N-C≡N or -N=C=N−) to yield the symmetric anion C
3(NCN)2−
3.
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