G. M. Kheifets, V. Gindin, E. P. Studentsov
Apr 1, 2006
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Journal
Russian Journal of Organic Chemistry
Abstract
Abstract5-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.