The extra lability (89 ×) of prostacyclin towards acid-catalysed hydrolysis of its vinyl ether functional group in aqueous solution at 25 °C is traced to the carboxylic acid residue of this molecule operating in its ionized form, either as an electrostatic catalyst or, upon prior protonation, as an intramolecular general acid catalyst.
Y. Chiang, A. J. Kresge and M. J. Cho, J. Chem. Soc., Chem. Commun., 1979, 129 DOI: 10.1039/C39790000129
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