Tautomerism of 5-fluoro-4-hydroxy-2-methoxypyrimidine. Conditions for stabilization of the zwitterionic tautomer

Article abstract of DOI:10.1134/S1070428006040166

5-Fluoro-4-hydroxy-2-methoxypyrimidine exists in a solution as two oxo tautomers with the conjugated and isolated double bonds in the ring. The latter tautomer has a zwitterionic structure, and it dominates in water and trifluoroethanol. 5-Fluoro-4-hydroxy-2-methoxypyrimidine in acidic medium gives rise to an equilibrium mixture of two protonated forms at a ratio of about ～1:1. The zwitterionic structure of 4-hydroxypyrimidines is stabilized if the solvent is capable for specific solvation via hydrogen bonding. Pleiades Publishing, Inc., 2006.

Full text of DOI:10.1134/S1070428006040166

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