Influence of one-electron oxidation and one-electron reduction on the tautomeric preferences for purine

Analytical and Bioanalytical Electrochemistry

Volumn 1, Issue 2, 2009, Pages 83-97

  Raczyńska, Ewa D ^a   Kamińska, Beata ^a   Szelag, MaŁgorzata ^a  

^a WARSAW UNIVERSITY OF LIFE SCIENCES   (Poland)

Author keywords

Charged radicals; Density functional theory (DFT); Effects of one electron reduction; Effects of one electronoxidation; NH and CH tautomers; Purine

Indexed keywords

EID: 77949329699     PISSN: None     EISSN: 20084226     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. J. S. Kwiatkowski, and B. Pullman, Adv. Heterocyclic Chem. 18 (1975) 199.
2. [J. S. Kwiatkowski, and W. B. Person, In Theoretical Biochemistry and Molecular Biology, D. L. Beveridge, and R. Lavery (Eds.), Academic Press, New York, 1990.
3. [J. Elguero, C. Marzin, A. R. Katritzky, and P. Linda, In Advances in Heterocyclic Chemistry, Supplement, A. R. Katritzky, and A. J. Boulton (Eds.), Academic Press, New York (1976).
4. A. F. Pozharskii, A. T. Soldatenkov, and A. R. Katritzky, Heterocycles in Life and Society, Wiley, New York, 1997;
5. A. R. Katritzky, K. Jug, and D. C. Oniciu, Chem. Rev. 101 (2001) 1421.
6. A. T. Balaban, D. C. Oniciu and A. R. Katritzky, Chem. Rev. 104 (2004) 2777.
7. J. A. Joule, and G. F. Smith, Heterocyclic Chemistry, Van Nostrand Reinhold Company, New York, 1978.
8. E. D. Raczyńska, W. Kosińska, B. Ośmiałowski, and R. Gawinecki, Chem. Rev. 105, 3561 (2005).
9. A. C. Borin, L. Serrano-Andrés, M. P. Fülscher, and B. O. Ross, J. Phys. Chem. A 103 (1999) 1838.
10. F. Pearl, and E. Gallego, Spectrochim. Acta A 56 (2000) 747.
11. T. Bartl, Z. Zacharova, P. Seckarova, E. Kolehmainen, and R. Marek, Eur. J. Org. Chem. (2009) 1377.
12. M. J. Nowak, H. Rostkowska, L. Lapinski, J. S. Kwiatkowski, and J. Leszczynski, J. Phys. Chem. 98 (1994) 2813.
13. N. El-Bakali Kassimi, and A. J. Thakkar, J. Mol. Struct. (Theochem) 366 (1996) 185.
14. W. Caminati, G. Maccaferri, P. G. Favero, and L. B. Favero, Chem. Phys. Lett. 251 (1996) 189.
15. A. Broo, and A. Holmén, Chem. Phys. 211 (1996) 147.
16. L. Houben, K. Schoone, J. Smets, L. Adamowicz, and G. Maes, J. Mol. Struct. 410-411 (1997) 397.
17. M. Szelag, and E. D. Raczyńska, Trends Org. Chem. 12 (2008) 19.
18. C. Chatigilialoglu, C. Caminal, A. Altieri, G. C. Vougioukalakis, Q. G. Mulazzani, T. Gimisis, and M. Guerra, J. Am. Chem. Soc. 128 (2006) 13796.
19. [X. Li, K. H. Bowen, M. Haranczyk, R. A. Bachorz, K. Mazurkiewicz, J. Rak, and M. Gutowski, J. Chem. Phys. 127 (2007) art. no. 174309.
20. M. Haranczyk, M. Gutowski, X. Li, and K. H. Bowen, J. Phys. Chem. B 111 (2007) 14076.
21. [R. G. Parr, and W. Yang, Density Functional Theory of Atoms and Molecular Orbital Theory, Oxford University Press, New York, 1989.
22. A. D. Becke, J. Chem. Phys. 98 (1993) 5648.
23. C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B 37 (1988) 785.
24. S. Bohm, P. Fiedler, and O. Exner, New J. Chem. 28 (2004) 67.
25. P. Fiedler, S. Bohm, J. Kulhanek, and O. Exner, Org. Biomol. Chem. 4 (2006) 2003.
26. O. Exner, and S. Bohm, Collect. Chech. Chem. Commun. 71 (2006) 1239.
27. W. J. Hehre, L. Radom, P. v. R. Schleyer, and J. A. Pople, Ab initio Molecular Theory, Wiley, New York, 1986.
28. F. Jensen, Introduction to Computational Chemistry, John Wiley & Sons, New York, 1999.
29. M. J. Firsch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Jr. Montgomery, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, R. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, R. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Oritz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian-03, Revision E.01, Gaussian, Inc., Wallingford CT, 2004.
30. D. G. Watson, R. M. Sweet, and R. E. Marsh, Acta Crystallogr. 19 (1965) 573.
31. O. Exner in Advances in Linear Free Energy Relationships, Plenum Press, London & New York, 1972, Ch. 1.
32. J. E. Lefler, and E. Grunwald, Rates and Equilibria of Organic Reactions, John Wiley and Sons, Inc., New York and London, 1963, Ch. 6.
33. W. G. Mallard, and P. J. Linstrom(eds),NIST Chemistry WebBook. NIST Standard Reference Database. National Institute of Standards and Thechnology, Gaithersburg, 2005.