May 20 2013
Tautomers are formed by an interconvertible reaction called tautomerization whereby there is a formal migration of a hydrogen atom along with a switch of a single bond and an adjacent double bond. A common example is the keto to enol tautomerism:
During tautomerization a chemical equilibrium of the tautomers will be reached based on several factors, including, pH, temperature and solvent. Tautomerizations are catalyzed by: bases (deprotonation, formation of a delocalized anion, and, protonation at a different position of the anion; and acids (protonation, formation of a delocalized cation, and deprotonation at a different position adjacent to the cation).
ICM will only generate energetically favorable tautomers. Generally tautomers that have a change in hybridization state are less stable and so ICM will not generate these thus reducing the number of scaffolds generated. For example the keto form shown below is more stable by ~14 kcal.mol than the enol therefore ICM will not generate the enol form.
To generate tautomeric conformations of your compound:
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