Ab initio study of the tautomeric forms of some quinolinediones

1995

Abstract 7,8-dihydroquinoline-4,5 (1 H ,6 H )-dione ( 1 ) and 7,8-dihydroquinoline-2,5-(1 H ,6 H )-dione ( 2 ) in their tautomeric oxo and hydroxy forms have been studied by ab initio Hartree-Fock calculations; tautomerization energies predict a more stable hydroxy structure having an intramolecular hydrogen bond for compound 1, whereas the oxo form is slightly-preferred for compound 2. Fourier Transform-Infra Red (FT-IR) spectra in CHCl 3 solution indicate that the predicted most stable tautomers in the vapour phase remain as such.