AM1 and PM3 Study of Tautomerism of Hypoxanthine in the Gas and Aqueous Phases

Structural Chemistry

Volumn 12, Issue 1, 2001, Pages 15-21

  Civcir, Pervin Ünal ^a  

^a ANKARA UNIVERSITY   (Turkey)

Author keywords

AM1, PM3 semiempirical calculation; Dipole moment; Hypoxanthine; Ionization potential; Tautomeric equilibrium constant; Tautomerism

Indexed keywords

EID: 0001788446     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1009253916904     Document Type: Article

References (39)

1. Hurst, D. T. An Introduction to the Chemistry and Biochemistry of Pyrimidines, Purines and Pteridines; John Wiley, New York, 1980, 179-203.
2. Rundless, R. W.; Wyngaarden, J. B.; Hitchings, G. H.; Elion, G. B.; Silberman, H. P. Trans. Assoc. Amer. Phys. 1963, 76, 126.
3. Elion, G. B.; Callahan, S.; Hitchings, G. H.; Rundles, R. W.; Laszlo, J. Cancer Chemother. Rept. 1962, 16, 1971.
4. Scanlan, M. J.; Hillier, I. H. J. Amer. Chem. Soc. 1984, 106, 3837.
5. Lin, J.; Yu, C.; Peng, S.; Akiyama, I.; Li, K.; Kao-Lee, L.; LeBreton, P. R. J. Phys. Chem. 1980, 84, 1006.
6. Sheina, G. C.; Stepanian, S. G.; Radchenko, E. D.; Blagoi, Y. P. J. Mol. Struct. (Theochem.) 1987, 158, 275.
7. Benoit, R. L.; Frechette, M. Can. J. Chem. 1985, 63, 3053.
8. Medeiros, G. C.; Thomas, G. J. J. Biochim. Biophys. Acta 1971, 238.
9. Lichtenberg, D.; Bergmann, F.; Neiman, Z. Isr. J. Chem. 1972, 10, 805.
10. Psoda, A.: Shugar, D. Biochim. Biophys. Acta 1971, 247, 507.
11. Chenon, M. T.; Pugmire, R. J.; Grant, D. M.; Panzica, R. P.; Townsend, L. B. J. Amer. Chem. Soc. 1975, 97, 4636.
12. Schmalle, H. W.; Hanggi, G.; Dubler, E. Acta. Crystallogr. 1988, C44, 732.
13. Dubler, E.; Hanggi, G.; Schmalle, H. W. Inorg. Chem. 1990, 29, 2518.
14. Izatt, R. M.; Christensen, J. J.; Ryttine, J. H. Chem. Rev. 1971, 71, 439.
15. Tauler, R.; Cid, J. F.; Casassas, E. J. Inorg. Biochem. 1990, 39, 277.
16. Pullman, B.; Pullman, A. Advan. Heterocyclic Chem. 1971, 13, 77.
17. Hernandez, B.; Luque, F. J.; Orozco, M. J. Org. Chem. 1996, 61, 5964.
18. Kassimi, N. El-B.; Thakkar, A. J. J. Mol. Struct. (Theochem.) 1996, 366, 185.
19. Nonella, M.; Hanggi, G.; Dubler, E. J. Mol. Struct. (Theochem.) 1993, 279, 173.
20. Contreras, J. G.; Alderere, J. B. Mole. Eng. 1992, 2, 29.
21. Civcir, P. U. J. Mol. Struct. (Theochem.) 2000, 532, 157.
22. Civcir, P. U. J. Mol. Struct. (Theochem.) (Ref. THEOCH6808), in press.
23. Civcir, P. U. J. Mol. Struvt. (Theochem.) Ref. THEOCH6850), in press.
24. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Amer. Chem. Soc. 1985, 107, 366.
25. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209.
26. Stewart, J. J. P., Mopac 7.0, Quantum Chemistry Program Exchange, University of Indiana, Bloomington, Indiana.
27. Klamt, A.; Schuurmann, G. J. Chem. Soc. Perkin Trans. 2 1993, 799.
28. CS Chem Office, Pro. for Microsoft Windows, Cambridge Scientific Computing, Inc., 875 Massachusetts Avenue, Suite 61, Cambridge, MA 02139, USA.
29. Mezey, P. G.; Ladik, J. J. Theoret. Chim. Acta 1979, 52, 129.
30. Mezey, P. G.; Ladik, J. J.; Barry, M. Theoret. Chim. Acta 1980, 54, 251.
31. Beak, P. Accounts Chem. Res. 1977, 10, 186.
32. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Amer. Chem. Soc. 1985, 107, 3902.
33. Stewart, J. J. P. J. Comp. Chem. 1989, 10, 221.
34. Beak, P.; White, J. M. J. Amer. Chem. Soc. 1982, 104, 7073.
35. Richards, W. G. Quantum Pharmacology, Butterworths & Co., London, 1983.
36. Aaron, J. J.; Gaye, M. D.; Parkanyi, C.; Cho, N. S.; Szentpaly, L. V. J. Mol. Struct. (Theochem.) 1987, 156, 275.
37. Shaw, G. Comprehensive Heterocyclic Chemistry: The Structures, Reactions, Synthesis and Uses of Heterocyclic Compounds A. R. Katritzky; W. Rees, eds.; Pergamon Press: Oxford, 1984; Vol. 5, p. 499.
38. Kwiatkowksi, J. S. Theoret. Chim. Acta 1968, 11, 167.
39. Dewar, M. J. S.; Yamaguchi, Y.; Doraiswamy, S.; Sharma, S. D.; Suck, S. H. Chem. Phys. 1979, 41, 21.