Quantum chemical studies on tautomerism of barbituric acid in gas phase and in solution.

Ab inito and density functional theory (DFT) methods were used to study the tautomers of barbituric acid in the gas phase and in a polar medium. In the gas phase, the tautomers were optimized at the HF/6-31G*, MP2/6-31G* and B3LYP/6-31G*, B3PW91/6-31G* levels of theory. The self-consistent reaction field theory (SCRF) at the HF/6-31G* level of theory has been used to optimize the tautomers in a polar medium. The relative stability of the tautomers was compared in the gaseous and polar mediums. The ability of maximum hardness principle to predict the stable tautomer has been studied. The 13C-NMR chemical shift for carbon atoms in the tautomers was calculated and the results are discussed.