Santonic acid

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Santonic acid
Santonic-acid-2D-skeletal.png Santonic-acid-from-xtal-3D-balls.png
Identifiers
PubChem 283654
ChemSpider 249878 YesY
Jmol-3D images Image 1
Properties
Molecular formula C15H20O4
Molar mass 264.32 g mol−1
Density 1.184 g cm−3[1]
Melting point 173 °C[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Santonic acid is an organic compound containing both carboxylic acid and ketone functionality.

It was synthesized from santonin by base-mediated hydrolysis of a lactone followed by a multistep rearrangement process by R. B. Woodward.[2]

Unusually for a carboxylic acid, santonic acid does not form hydrogen-bonded dimers in the crystalline phase. Rather, it adopts a polymeric structure, with individual santonic acid molecules linked by intermolecular carboxyl-to-ketone hydrogen bonds.[1]

References[edit]

  1. ^ a b c A. P. J. Brunskill, H. W. Thompson and R. A. Lalancette (April 1999). "Santonic acid: catemeric hydrogen bonding in a γ,ε-diketo carboxylic acid". Acta Cryst. C55 (4): 566–568. doi:10.1107/S0108270198014231. 
  2. ^ Reusch, William (1999). "Base-catalyzed rearrangements". In: Virtual Textbook of Organic Chemistry. Michigan State University. Retrieved September 10, 2008.