Dimer Mechanism for the Tautomeric Conversion of 4-Amino-2-oxopyrimidine

Quantum-chemical description of the prototropic tautomerism of pyrimidine bases

“…Prototropic tautomerism in nitrogen-containing heteroaromatic compounds has been well studied by experimental [1][2][3][4] and theoretical [5][6][7][8][9][10][11] methods, and general conclusions have been drawn that tautomeric keto and amino forms are canonical, the equilibrium constant depends on the structure of the compound and the solvent, and proton transfer is effected according to a cyclic dimer mechanism. Particular attention has been paid to the study of tautomeric conversions of pyrimidine bases with the aim of a qualitative description of the uncommon tautomeric forms and processes [12][13][14][15][16], and also clarification of the possibility of the existence of intermolecular hydrogen bonds [17][18][19].…”