Molecule of the Week

Meldrum’s Acid

April 12, 2010

In 1908, A. N. Meldrum condensed malonic acid with acetone to produce a compound he misidentified as a carboxylic acid—hence the name “Meldrum’s acid”. Not until 1948 did D. Davidson and S. A. Bernhard show that the compound has the dioxane-dione structure shown here. Its acidity derives from the lability of the hydrogen atoms between the carbonyl groups. The same authors noted that Meldrum’s acid is a ketene precursor. Recently B. Moon and C. J. Hawker used this property to create polymers with reactive ketene substituents.