Abstract
Values of the enthalpy (ΔH), 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.
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REFERENCES
A. Buda and A. Syqula, J. Mol. Struct. (Theochem), 92, 255 (1985).
U. Norinder, J. Mol. Struct. (Theochem), 151, 259 (1987).
P. U. Civcir, J. Mol. Struct. (Theochem), 532, 157 (2000).
M. Shibata, T. J. Zielinski, and R. Rein, Int. J. Quant. Chem., 18, 323 (1980).
T.-K. Ha and H. H. Guntard, J. Am. Chem. Soc., 115, 11939 (1993).
T.-K. Ha, H.-J. Keller, R. Gunde, and H. H. Guntard, J. Phys. Chem. A, 103, 6612 (1999).
A. R. Katritzky, M. Karelson, and P. A. Harris, Heterocycles, 32, 329 (1991).
C. Colominas, F. J. Luque, and M. Orozco, J. Am. Chem. Soc., 118, 6811 (1996).
A. Destexhe, J. Smets, L. Adamowicz, and G. Meas, J. Am. Chem. Soc., 116, 1506 (1994).
A. E. Porter, in: General Organic Chemistry, Vol. 8, Khimiya, Moscow (1985), p. 131.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 564–568, April, 2005.
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Churgulia, E.J., Kereselidze, J.A. Dimer Mechanism for the Tautomeric Conversion of 4-Amino-2-oxopyrimidine. Chem Heterocycl Compd 41, 481–484 (2005). https://doi.org/10.1007/s10593-005-0175-7
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DOI: https://doi.org/10.1007/s10593-005-0175-7