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Ab initio study of the tautomeric forms of some quinolinediones
Authors:Monica Bartolomei   Maurizio Cignitti   Marina Cotta Ramusino  Gianfranco La Manna  
Affiliation:

aIstituto Superiore di Sanità, Laboratorio di Chimica del Farmaco, Viale Regina Elena 299, 00161 Roma, Italy

bDipartimento di Chimica Fisica, Gruppo Chimica Teorica, Università, Via Archirafi 20, 90123 Palermo, Italy

Abstract:7,8-dihydroquinoline-4,5 (1H,6H)-dione (1) and 7,8-dihydroquinoline-2,5-(1H,6H)-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 CHCl3 solution indicate that the predicted most stable tautomers in the vapour phase remain as such.
Keywords:
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