Steric and electronic effects in imine-hemiaminal ring-chain tautomerism

Article abstract of DOI:10.1016/S0040-4020(96)00352-3

We have examined a series of 1,3-dihydro-1-isobenzofuranamines that exist in an imine/hemiaminal ring-chain tautomerism. The tautomeric free energies are rationalized in terms of electronic and steric effects. A series of compounds bearing substituents of varying bulk have free energies that correlate well with substituent A values.