Comparisons of equilibrium constants for the hydration of alkenes to form alcohols and of enols to form gem diols show that an oxygen substituent favours hydration as a result of the stabilising geminal interaction of carbon–oxygen bonds in the diol; oxygen substituent effects on other H–X addition equilibria (e.g. HNMe2, HSEt) measure the strength of ‘geminal’ C–O/C–X interactions.
M. P. Harcourt and R. A. M. O'Ferrall, J. Chem. Soc., Chem. Commun., 1987, 823 DOI: 10.1039/C39870000823
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