Hydrogen-transferred radical cations of NADH model compounds. 3. 1,8-Acridinediones

Journal of Physical Chemistry A

Volumn 104, Issue 4, 2000, Pages 724-728

  Marcinek, Andrzej ^a   Adamus, Jan ^b   Gçbicki, Jerzy ^c   Platz, Matthew S ^a   Bednarek, Pawet ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

^b OHIO STATE UNIVERSITY   (United States)

^c UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001371716     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp993817r     Document Type: Article

References (31)

1. Gȩbicki, J.; Marcinek, A.; Adamus, J.; Paneth, P.; Rogowski, J. J. Am. Chem. Soc. 1996, 118, 691.
2. Marcinek, A.; Adamus, J.; Huben, K.; Gȩbicki, J.; Bartczak, T. J.; Bednarek, P.; Bally, T. J. Am. Chem. Soc., in press.
3. Marcinek, A.; Rogowski, J.; Adamus, J.; Gȩbicki, J.; Bednarek, P.; Bally. T. J. Phys. Chem. A 2000, 104, 718.
4. Singh, S.; Chhina, S.; Sharma, V. K. J. Chem. Soc., Chem. Commun. 1982, 453.
5. Mohan, H.; Srividya, N.; Ramamurthy, P.; Mittal, J. P. J. Chem. Soc., Faraday Trans. 1996, 92, 2353.
6. Mohan, H.; Mittal, J. P.; Venkatachalapathy, B.; Srividya, N.; Ramamurthy, P. J. Chem. Soc., Faraday Trans. 1997, 93, 4269.
7. Mohan, H.; Srividya, N.; Ramamurthy, P.; Mittal, J. P. J. Phys. Chem. A 1997, 101, 2931.
8. Mohan, H.; Mittal, J. P.; Srividya, N.; Ramamurthy, P. J. Phys. Chem. A 1998, 102, 4444.
9. Shida, T. Electronic absorption spectra of radical ions', Elsevier: Amsterdam, 1988.
10. Marcinek, A.; Rogowski, J.; Adamus, J.; Gȩbicki, J.; Platz, M. S. J. Phys. Chem. 1996, 700, 13539.
11. Bednarek, P.; Gȩbicki, J.; Bally, T. Unpublished results.
12. Assignment of the 680 nm absorption band to the primary radical cation could be incorrect only if one assumes its fast intramolecular transformation. Also a high degree of aggregation of neutral compound prior to ionization could facilitate proton transfer within ionized aggregates and radical formation. An assignment of this band to the radical would imply instability of the initially formed radical cation, in contrast to the observed stability of the species absorbing at 550 nm. Moreover, it would also support an assignment of the latter species to the more stable enol radical cation.
13. For reasons of computational economy all calculations presented in this study and related to 1HK were limited to the 10-methyl-3,4,6,7,9,10hexahydro-l,8(2H,5H)-acridinedione (i.e., without four methyl. groups attached to 3 and 6 positions of side rings).
14. Land, E. J.; Swallow, A. J. Biochim. Biophys. Acta 1968, 762,327.
15. Brühlmann, U.; Hayon, E. J. Am. Chem. Soc. 1974, 96, 6169.
16. Kosower, E. M.; Teuerstein, A.; Burrows, H. D.; Swallow, A. J. J. Am. Chem. Soc. 1978, 700, 5185.
17. Srividya, N.; Ramamurthy, P.; Shanmugasundaram, P.; Ramakrishnan, V. T. J. Org. Chem. 1996, 61, 5083.
18. The symbol for this compound matches the nomenclature of refs 2 and 3.
19. Timpe, H.-J.; Ulrich, S.; Fouassier, J.-P. J. Photochem. Photobiol. A 1993, 73, 139.
20. Srividya, N.; Ramamurthy, P.; Ramakrishnan, V. T. Spectrochim. Acta A 1998, 54, 245.
21. Karolczak, S.; Hodyr, K.; lubis. R.; Kroh, J. J. Radioanal Nucl. Chem. 1986, 707, 177.
22. Gȩbicki, J.; Marcinek, A.; Rogowski, J. Radiat. Phys. Chem. 1992, 39, 41.
23. Gritsan, N. P.; Zhai, H. B.; Yuzawa, T.; Karweik, D.; Brooke, J.; Platz, M. S. J. Phys. Chem. A 1997, 707, 2833.
24. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
25. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
26. 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.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. 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.; HeadGordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, revisions Bl and D4; Gaussian, Inc.: Pittsburgh, PA, 1995.
27. For a description of the DFT methods implemented in the Gaussian program, see the following. Johnson, B. G.; Gill, P. M. W.; Pople, J. A. J. Chem. Phys. 1993, 98, 5612.
28. Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 709, 8218.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; ' Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, L; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision AS; Gaussian, Inc.: Pittsburgh, PA, 1998.
30. Bally, T.; Albrecht, B.; Matzinger, S.; Sastry, M. G.: MOPLOT (a program for displaying results of LCAO-MO calculations), version 3.2; University of Fribourg, Switzerland, 1997. Available from Thomas.Bally@unifr.ch on request.
31. Haselbach, E.; Schmelzer, A. Helv. Chim. Acta 1979, 54, 1299.