DIMER MECHANISM FOR THE TAUTOMERIC CONVERSION OF 4-AMINO-2-OXOPYRIMIDINE
DOI:
https://doi.org/10.1007/8326Keywords:
cytosine, pyrimidine, molecular rearrangement, quantum-chemical calculations, tautomeric conversionsAbstract
Values of the enthalpy (∆H), atomic charges (qi), and bond orders (Pij) for six tautomeric forms of 4-amino-2-oxopyrimidine have been calculated by the semiempirical AM1 quantum-chemical method. It was found that the most stable of these is 4-amino-2-oxo-1H-pyrimidine (cytosine). By analogy with complementary pairs of nucleotide bases, the tautomeric conversion of cytosine and other oxo forms can come about via a dimeric intermolecular mechanism. A novel interpretation is proposed for the conversion of cytosine to 4-amino-2-oxo-3H-pyrimidine as a result of a 1H-3H two stage proton transfer.How to Cite
Churgulia, E. J.; Kereselidze, J. A. Chem. Heterocycl. Compd. 2005, 41, 481. [Khim. Geterotsikl. Soedin. 2005, 564.]
For this article in the English edition, see DOI 10.1007/s10593-005-0175-7
