Sometimes, a 'cosmetic' software enhancement provides new insights of the sort described by Marcel Proust:'The voyage of discovery is not in seeking new landscapes but in having new eyes.'Tautomerism is so crucial that two years ago an entire ACS Symposium was dedicated to the topic. At that time, we cited the lack of a comprehensive database of tautomeric constants as the main obstacle in developing quantitative predictive models of tautomerism. We also set out the mathematical relationships between tautomeric and ionization equilibria in special cases when a common cation or anion is involved. Subsequent analysis triggered by the new insight has revealed a deeper relationship between ionization and tautomerism than previously understood, showing the way to construct a _full_ tautomeric model from abundant ionization data. Here, we present the theory behind this model as well as some preliminary applications.

Return of the tautomers: Toward a global model of tautomerism

245th National Meeting (2013)

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