Theoretica chimica acta

, Volume 52, Issue 2, pp 129–145 | Cite as

A non-empirical molecular orbital study on the relative stabilities of adenine and guanine tautomers

  • Paul G. Mezey
  • Janos J. Ladik
Original Investigations


The relative stabilities of a series of adenine and guanine tautomers have been calculated using anab initio Hartree-Fock-Roothaan SCF MO method. The calculated relative stabilities agree in general with the results of earlier semiempirical studies. According to the present study, tautomeric forms with regular Kekulé structure for the six-membered purine ring are the most stable. The amine-imine tautomerization of purine bases is not likely to be responsible for spontaneous mutations in DNA.

Key words

Adenine tautomers, relative stabilities of ∼ Guanine tautomers, relative stabilities of ∼ 


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  1. 1.
    Jordan, D. O.: The chemistry of nucleic acids. London: Butterworths 1960; Ulbricht, T. L. V.: Purines, pyrimidines and nucleotides, and the chemistry of nucleic acids. New York: Pergamon Press 1964Google Scholar
  2. 2.
    Goddard, J. D., Mezey, P. G., Csizmadia, I. G.: Theoret. Chim. Acta (Berl.)39, 1 (1975)Google Scholar
  3. 3.
    Hoffman, T. A., Ladik, J.: Advan. Chem. Phys.7, 84 (1964); Ladik, J., Appel, K.: Theoret. Chim. Acta (Berl.)4, 132 (1966)Google Scholar
  4. 4.
    Strickberger, M. W.: Genetics. New York: Macmillan and Co. 1968Google Scholar
  5. 5.
    Watson, J. D.: The molecular biology of the gene, 2nd ed. New York: Benjamin 1970Google Scholar
  6. 6.
    Angell, C. L.: J. Chem. Soc.504 (1961)Google Scholar
  7. 7.
    Marshall, J. R., Walker, J.: J. Chem. Soc.1004 (1951)Google Scholar
  8. 8.
    Shugar, D., Fox, J. J.: Biochim. Biophys. Acta9, 199 (1952)Google Scholar
  9. 9.
    Brown, D. J., Lyall, J. M.: Aust. J. Chem.15, 851 (1962)Google Scholar
  10. 10.
    Clark, L. B., Tinoco, I.: J. Am. Chem. Soc.87, 11 (1965)Google Scholar
  11. 11.
    Maevskii, A. A.: Biofizika20, 957 (1975)Google Scholar
  12. 12.
    Spencer, M.: Acta Cryst.12, 59 (1959)Google Scholar
  13. 13.
    Arnott, S., Dover, S. D., Wonacott, A. J.: Acta Cryst.B25, 2192 (1969)Google Scholar
  14. 14.
    Blout, E. R., Fields, M.: J. Am. Chem. Soc.72, 479 (1950)Google Scholar
  15. 15.
    Kokks, J. P., Goldstein, J. H., Mandell, L.: J. Am. Chem. Soc.83, 2909 (1961)Google Scholar
  16. 16.
    Austin, J. E.: J. Am. Chem. Soc.56, 2141 (1934)Google Scholar
  17. 17.
    Tanaka, M., Nagakura, S.: Theoret. Chim. Acta (Berl.)6, 320 (1966)Google Scholar
  18. 18.
    Morita, H., Nagakura, S.: Theor. Chim. Acta (Berl.)11, 279 (1968)Google Scholar
  19. 19.
    Pullman, B., Pullman, A.: Quantum biochemistry. New York-London: Academic Press 1963; Yu, C., Peng, S., Akiyama, I., Lin, J., LeBreton, P. R.: J. Am. Chem. Soc.100, 2303 (1978)Google Scholar
  20. 20.
    Clark, L. B., Peschel, G. G., Tinoco, I., Jr.: J. Phys. Chem.69, 3615 (1965)Google Scholar
  21. 21.
    Boerresen, H. C.: Acta Chim. Scand.21, 2463 (1967)Google Scholar
  22. 22.
    Berthod, H., Giessner-Prettre, C., Pullman, A.: Theoret. Chim. Acta (Berl.)5, 53 (1966)Google Scholar
  23. 23.
    Fujita, H., Imamura, A., Nagata, C: Bull. Chem. Soc. Jap.42, 1467 (1969)Google Scholar
  24. 24.
    Ladik, J., Biczó, G., Rédly, J.: Phys. Rev.188, 710 (1969)Google Scholar
  25. 25.
    Breen, D. L., Flurry, R. L.: Theoret. Chim. Acta (Berl.)23, 138 (1971)Google Scholar
  26. 26.
    Giessner-Prettre, C., Pullman, A.: Theoret. Chim. Acta (Berl.)9, 242 (1968); Pullman, A., Kochanski, E., Gilbert, M., Denis, A.: Theoret. Chim. Acta (Berl.)10, 231 (1968)Google Scholar
  27. 27.
    Pullman, B., Berthod, H., Dreyfuß, M.: Theoret. Chim. Acta (Berl.)15, 265 (1969); Pullman, B., Berthod, H., Bergmann, F., Neiman, Z., Weiler-Feilchenfeld, H., Bergmann, E. D.: Tetrahedron26, 1483 (1970)Google Scholar
  28. 28.
    Kwiatkowski, J. S.: Theoret. Chim. Acta (Berl.)13, 149 (1969)Google Scholar
  29. 29.
    Bodor, N., Dewar, M. J. S., Harget, A. J.: J. Am. Chem. Soc.92, 2929 (1970)Google Scholar
  30. 30.
    Hug, W., Tinoco, I, Jr.: J. Am. Chem. Soc.95, 2803 (1973)Google Scholar
  31. 31.
    Hug, W., Tinoco, I, Jr.: J. Am. Chem. Soc.96, 665 (1974)Google Scholar
  32. 32.
    Ladik, J., in: Electronic structure of polymers and molecular crystals, André, J.-M. and Ladik, J., eds., p. 663. New York: Plenum Press 1975Google Scholar
  33. 33.
    Clementi, E., André, J.-M., André, M.-Cl., Klint, D., Hahn, D.: Acta Phys. Hungarian Acad. Sci.27, 493 (1969)Google Scholar
  34. 34.
    Clementi, E., Mehl, J., Niessen, W.: J. Chem. Phys.54, 508 (1971)Google Scholar
  35. 35.
    Mely, B., Pullman, A.: Theoret. Chim. Acta (Berl.)13, 278 (1969)Google Scholar
  36. 36.
    Ladik, J., Suhai, S., Otto, P., Collins, T. C.: Intern. J. Quantum Chem. Quant. Biol. Symp.4, 55 (1977)Google Scholar
  37. 37.
    Suhai, S., Merkel, Ch., Ladik, J.: Phys. Letters61A, 487 (1977)Google Scholar
  38. 38.
    Szent-Györgyi, A.: Bioelectronics4, 535 (1973); Szent-Györgyi, A.: Acta Biochem. Biophys. Acad. Sci. Hung.8, 117 (1973); Szent-Györgyi, A.: Life Sci.15, 863 (1977)Google Scholar
  39. 39.
    Ladik, J.: Intern. J. Quantum Chem. Quantum Biol. Symp.1, 65 (1974)Google Scholar
  40. 40.
    Laki, J.: Intern. J. Quantum Chem. Quantum Biol. Symp.2, 133 (1975)Google Scholar
  41. 41.
    Laki, K., Ladik, J.: Intern. J. Quantum Chem. Quantum Biol. Symp.3, 51 (1976)Google Scholar
  42. 42.
    Roothaan, C. C. J.: Rev. Mod. Phys.23, 69 (1951)Google Scholar
  43. 43.
    Hehre, W. J., Lathan, W. A., Ditchfield, R., Newton, M. D., Pople, J. A.: QCPE program 236, Indiana University, Bloomington, IndianaGoogle Scholar
  44. 44.
    Hehre, W. J., Stewart, R. F., Pople, J. A.: J. Chem. Phys.51, 2657 (1969)Google Scholar
  45. 45.
    Kapur, A., Steer, R. P., Mezey, P. G.: J. Chem. Phys.69, 968 (1978)Google Scholar
  46. 46.
    Mezey, P. G.: Chem. Phys. Letters47, 70 (1977)Google Scholar

Copyright information

© Springer-Verlag 1979

Authors and Affiliations

  • Paul G. Mezey
    • 1
    • 2
  • Janos J. Ladik
    • 3
    • 4
  1. 1.Department of Chemistry and Chemical EngineeringUniversity of SaskatchewanSaskatoonCanada
  2. 2.Laboratory of the National Foundation for Cancer Research at the Chair of Theoretical ChemistryUniversity of Erlangen-NürnbergCanada
  3. 3.Chair of Theoretical ChemistryUniversity of Erlangen-NürnbergGermany
  4. 4.Laboratory of the National Foundation for Cancer Research at the Chair of Theoretical ChemistryUniversity of Erlangen-NürnbergErlangenGermany

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