Prototropic equilibria in 4-thiouracil: A combined spectroscopic and ab initio SCF-MO investigation

Journal of Physical Chemistry A

Volumn 102, Issue 12, 1998, Pages 2194-2200

  Rubin, Yuri V ^a   Morozov, Yuri ^b   Venkateswarlu, Divi ^c   Leszczynski, Jerzy ^c  

^a B VERKIN INSTITUTE FOR LOW TEMPERATURE PHYSICS AND ENGINEERING   (Ukraine)

^b ENGELHARDT INSTITUTE OF MOLECULAR BIOLOGY   (Russian Federation)

^c JACKSON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84961983626     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9726798     Document Type: Article

References (69)

1. (a) See, e.g.: Saenger, W. Principles of Nucleic Acid structure; Springer-Verlag: New York, 1984.
2. (b) Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structure; Springer-Verlag: New York, 1991.
3. (a) Charbonneau, H.; Beier, N.; Walsh, K. A.; Beavo, J. A. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 9308.
4. (b) Wells, J. N.; Garst, J. E.; Kramer, G. L. J. Med. Chem. 1981, 24, 954.
5. (a) Topiol, S.; Weinstein, H.; Osman, R. J. Med. Chem. 1981, 24, 954.
6. (b) Weinstein, H.; Mazurek, A. P.; Osman, R.; Topiol, S. Mol. Pharmacol. 1986, 29, 28.
7. (c) Osman, R.; Weinstein, H.; Topiol, S.; Rubenstein, L. Clin. Physiol. Biochem. 1985, 3, 80.
8. (d) Osman, R.; Topiol, S.; Rubenstein, L.; Weinstein, H. Mol. Pharmacol. 1987, 32, 699.
9. (e) Topiol, S. Trends Biochem. Sci. 1987, 12, 419.
10. (a) Hunter, C. J.; Deen, D. F.; Marton, L. J. Int. J. Cancer 1989, 44, 658.
11. (b) Pieters, R.; Huismans, D. R.; Loonen, A. H.; Hahlen, K.; Veerrnan, A. J. P. Jpn. J. Cancer Res. 1991, 82, 1051.
12. (c) Hunter, C. J.; Deen, D. F.; Marton, L. J. Int. J. Cancer 1989, 44, 658.
13. (d) Phillips, M. D.; Nascimbeni, B.; Tice, R. R.; Shelby, M. D. Environ. Mol. Mutagen. 1991, 18,168.
14. (e) Pieters, R.; Huismans, D. R.; Loonen, A. H.; Peters, G. J.; Hahlen, K.; Vander Does-van den Berg, A.; VanWeiring, E. R.; Veerman, A. J. P. Int. J. Cancer 1992, 51, 213.
15. (f) Bugg, C. E.; Thewald, U. J. Am. Chem. Soc. 1970, 92, 7441.
16. (a) Ruyle, W. V.; Shen, T. Y. J. Med. Chem. 1967, 10, 331.
17. (b) Beuachamp, L. M.; Serling, B. L.; Kesley, J. E;. Biron, K. K;. Collins, P.; Selway, J.; Lin, J. C.; Schaeffer, H. J. J. Med. Chem. 1988, 31, 144.
18. (c) Zingaro, R. A., Cooper, W. C., Eds.; Selenium; Van Nostrand Reinhold: New York, 1974. Patai, S., Rappoport, Z., Eds.; The Chemistry Organic Selenium and Tellurium Compounds; Wiley: New York, 1986; Vol. 1.
19. (c) Zingaro, R. A., Cooper, W. C., Eds.; Selenium; Van Nostrand Reinhold: New York, 1974. Patai, S., Rappoport, Z., Eds.; The Chemistry Organic Selenium and Tellurium Compounds; Wiley: New York, 1986; Vol. 1.
20. Lange, P. Antimetabolites of Nucleic Acid Metabolism, Gordon and Breach: New York, 1975.
21. Melvin, J, B.; Haight, T. H.; Leduc, E. H., Cancer Res. 1984, 44, 2794.
22. Sax, N. I.; Lewis, R. J., Sr. Dangerous Properties of Industrial Materials; Van Nostrand Reinhold: New York, 1989.
23. McEvoy, G. K., Ed. AHFS Drug Information, American Society of Hospital Pharmcists, Inc.: Bethesda, MD, 1989.
24. (a) Kwiatkowski, J. S.; Person, W. B.; Szczepaniak, K.; Szczesniak, M. Acta Biochim. Polon. 1987, 34, 165.
25. (b) Szczesniak, M.; Szczepaniak, K.; Kwiatkowski, J. S.; KuBulat, K.; Person, W. J. Am.Chem. Soc. 1988, 110, 8319.
26. (c) Nowak, M. J.; Lapinski, L.; Fulara, J. Spectrochim. Acta 1989, 45A, 229.
27. (d) Gould, I. R.; Vincent, M. A.; Hillier, I. H.; Lapinski, L.; Nowak, M. J. Spectrochim. Acta 1992, 48A, 811.
28. (e) Jaworski, A.; Szczesniak, M.; Szczepaniak, K.; KuBulat, K.; Person, W. B. J. Mol. Stract. 1990, 223, 63.
29. Winckelmann, I.; Larsen, E. H. Synthesis 1986, 1041.
30. Rostkowska, H.; Szczepaniak, K.; Nowak, J. M.; Leszczynski, J.; KuBulat, K.; Person, W. B. J. Am. Chem. Soc. 1990, 112, 2147.
31. (a) Leszczynski, J.; Lammertsma, K. J. Chem. Phys. 1991, 95, 3128.
32. (b) Szczepaniak, K.; Szczesniak, M.; Szajda, W.; Leszczynski, J.; Person, W. B. Can. J. Chem. 1991, 69, 1705.
33. (a) Leszczynski, J. J. Chem. Phys. 1992, 96, 1649.
34. (b) Leszczynski, J. Int. J. Quantum Chem. Quantum Biol. Symp. 1991, 18, 9.
35. Gould, I. R.; Burton, N. A.; Hall R. J.; Hillier, I. H. J. Mol. Struct.: THEOCHEM 1995, 331, 147.
36. Kwiatkowski, J. S.; Leszczynski, J. J. Phys. Chem. 1996, 100, 941.
37. Wang, Z.; Rana T. M. Biochemistry 1996, 35, 6491.
38. Martin, R. P.; Schneller, J. M.; Stahl, A. J. C.; Dirheimer, G. Biochem. Biophys. Res. Commun. 1976, 70, 997.
39. Altweg, M.; Kubli, E. Nucleic Acids. Res. 1980, 8, 215.
40. Dzik, J. M.; Bretner, M.; Kulikowski, T.; Golos, B.; Jarmula, A.; Ptznanski, J.; Rode, W.; Shugar, D. Biochem. Biophys. Acta. 1996, 1293, 1.
41. Les, A.; Adamowicz, L. J. Am. Chem. Soc. 1990, 112, 1504.
42. Elguero, J.; Marzin, C.; Kantrizky, A. R.; Linda, P. The tautomerism of heterocycles; Katritzky, A. R., Boulton, A. J., Eds.; Advances in Heterocyclic Chemistry, Suppl I; Academic Press: New York, 1976.
43. Rubin, Yu.V.; Savin, F. A.; Blagoi, Yu.P. Stud. Biophys. 1988, 123, 203.
44. Avdeenco, A. A. In Organische Halbleiter, Karl-Stadt, 1981; p 74.
45. See, for example: Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory, Wiley, New York, 1986.
46. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Oritiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E.I; Gaussian, Inc.: Pittsburgh PA, 1995.
47. Cramer, C. J.; Hawkins, G. D.; Lynch, G. C.; Giesen, D. J.; Truhlar, D. G.; Liotard, D. A.; AMSOL 4.5.1; QCPE program 606, version 4.5.
48. Cramer, C. J.; Truhlar, D. G. Science 1992, 256, 213.
49. (a) Cramer, C. J.; Truhlar, D. G. J. Comput. Chem. 1992, 13, 1089.
50. (b) Cramer, C. J.; Truhlar, D. G. J. Comput.-Aided Mol. Des. 1992, 6, 629.
51. Hernandez, B.; Orozco, M.; Luque, F. J. J. Comput.-Aided Mol. Des. 1996, 10, 535. Herandez, B.; Orozco, M.; Luque, F. J. J. Comput.-Aided Mol. Des. 1997, 11, 153. Hemandez, B.; Luque, F. J.; Orozco, M. J. Org. Chem. 1996, 61, 5964.
52. Hernandez, B.; Orozco, M.; Luque, F. J. J. Comput.-Aided Mol. Des. 1996, 10, 535. Herandez, B.; Orozco, M.; Luque, F. J. J. Comput.-Aided Mol. Des. 1997, 11, 153. Hemandez, B.; Luque, F. J.; Orozco, M. J. Org. Chem. 1996, 61, 5964.
53. Hernandez, B.; Orozco, M.; Luque, F. J. J. Comput.-Aided Mol. Des. 1996, 10, 535. Herandez, B.; Orozco, M.; Luque, F. J. J. Comput.-Aided Mol. Des. 1997, 11, 153. Hemandez, B.; Luque, F. J.; Orozco, M. J. Org. Chem. 1996, 61, 5964.
54. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.
55. Baranov, V. I.; Savin, F. A.; Gribov, L. A. Programma rascheta electronno-kolebatelnich spectrovmnogoatomnih molecul; M. Nauka: Moscow, 1983.
56. Rubin, Yu.V.; Bokovoi, V. A.; Blagoi, Yu.P. J. Fluoresc. 1995, 5, 263.
57. Bokovoi, V. A.; Morozov, Yu.V.; Bazhulina, N. P.; Chekhov, V. O. J. Phys. Khem. 1991, 65, 865.
58. (a) Leszczynski, J.; Sponer, J. J. Mol. Struct.: THEOCHEM 1996, 388, 237.
59. (b) Leszczynski, J. J. Phys. Chem. 1992, 96, 1649.
60. Stewart, M. J.; Leszczynski, J.; Rubin, Y. V.; Blagoi, Y. P. J. Phys. Chem. 1997, 101, 4753.
61. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: New York, 1990; pp 98-104.
62. Beak, P. Acc. Chem. Res. 1977, 10, 186.
63. Gorb, L.; Leszczynski, J. J. Am. Chem. Soc. 1998, in press.
64. Psoda, A.; Kazimierczuk Z.; Shugar D. J. Am. Chem. Soc. 1974, 96, 6832.
65. Lancelot, G. Mol. Phys. 1976, 31, 241-254.
66. Taherian, M. R.; Maki, A. H. Chem. Phys. 1981, 55, 85.
67. Shalitin, N.; Feitelson, J. J. Chem. Phys. 1973, 59, 1045.
68. Rubin, Yu.V.; Savin, F. A.; Chekhov, V. Ä. Biofyzica 1985, 30, 363.
69. Morozov, Yu.V.; Bazgulina, N. P. Electronnoje stroyenije, spectroscopija i reactseonnaja sposobnost' molekul; M. Nauka: Moscow, 1989.