EPR and MO calculation studies on α-aminoanthraquinone anion radicals in aprotic solvents

Magnetic Resonance in Chemistry

Volumn 37, Issue 11, 1999, Pages 774-780

  Vatanen, Virpi ^a   Eloranta, Jussi M ^a   Vuolle, Mikko ^a  

^a UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

Aminoanthraquinone; Anion radical; DFT; EPR; SCI PCM

Indexed keywords

CONTINUUM MECHANICS; ELECTRON SPIN RESONANCE SPECTROSCOPY; KETONES; NEGATIVE IONS;

AMINOANTHRAQUINONE; ANION RADICALS; APROTIC SOLVENTS; DFT; EPR SPECTRUM; HYPERFINE COUPLING CONSTANTS; ISODENSITY; MOLECULAR ORBITAL CALCULATIONS; POLARIZED CONTINUUM MODELS; SELF-CONSISTENT ISODENSITY POLARIZED CONTINUUM MODEL;

MOLECULAR ORBITALS;

EID: 0033229068     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-458X(199911)37:11<774::AID-MRC549>3.0.CO;2-1     Document Type: Article

References (60)

1. 1. J. Q. Chambers, in The Chemistry of Quinoid Compounds, edited by S. Patai and Z. Rappoport, Vol. II, p. 719. Wiley, Chichester (1988).
2. 2. D. Voet and J. G. Voet, Biochemistry. Wiley, New York (1995).
3. 3. R. H. Thomson, Naturally Occurring Quinones. Academic Press, London (1971).
4. 4. H. D. H. Showalter, D. W. Fry, W. R. Leopold, J. W. Lown, J. A. Plambeck and K. Reszka, Anti-Cancer Drug Des. 1, 73 (1986).
5. 5. B. Nguyen and P. L. Gutierrez, Chem.-Biol. Interact. 74, 139 (1990).
6. 6. S. D. Popescu and E. Barbacaru, Anal. Lett. 18, 947 (1985).
7. 7. K. Reszka, P. Kolodziejczyk and J. W. Lown, J. Free Rad. Biol. Med. 2, 25 (1986).
8. 8. A. E. Luytzkii and I. S. Romodanov, Teor. Eksp. Khim. 2, 830 (1966).
9. 9. K. Yasukouchi, H. Yamaguchi and S. Nagayama, Nippon Kagaku Zasshi 91, 213 (1970); I. S. Romodanov, N. A. Arshava, N. M. Kotelevskii and A. E. Lyutzkii, Vestn. Khar'k. Politekh. Ins. 92, 6 (1974).
10. 9. K. Yasukouchi, H. Yamaguchi and S. Nagayama, Nippon Kagaku Zasshi 91, 213 (1970); I. S. Romodanov, N. A. Arshava, N. M. Kotelevskii and A. E. Lyutzkii, Vestn. Khar'k. Politekh. Ins. 92, 6 (1974).
11. 10. J. A. Pedersen, J. Chem. Soc., Faraday Trans, 1 84, 3223 (1988); M. Ciureanu, M. Constantinescu and A. Meghea, Rev. Roum. Chim. 34, 1491 (1989); H. Bock, B. Hierholtzer and P. Schmalz, Angew. Chem. 99, 811 (1987).
12. 10. J. A. Pedersen, J. Chem. Soc., Faraday Trans, 1 84, 3223 (1988); M. Ciureanu, M. Constantinescu and A. Meghea, Rev. Roum. Chim. 34, 1491 (1989); H. Bock, B. Hierholtzer and P. Schmalz, Angew. Chem. 99, 811 (1987).
13. 10. J. A. Pedersen, J. Chem. Soc., Faraday Trans, 1 84, 3223 (1988); M. Ciureanu, M. Constantinescu and A. Meghea, Rev. Roum. Chim. 34, 1491 (1989); H. Bock, B. Hierholtzer and P. Schmalz, Angew. Chem. 99, 811 (1987).
14. 11. D. S. Ksenzek, S. A. Petrova, S. V. Oleynik, M. V. Kolodgazhnyi and V. Z. Moskovskii, Spektrokhimiya, 13, 182 (1977); E. McAlpine, R. S. Sinclair and T. G. Truscott, J. Chem. Soc., Faraday Trans. I 74, 597 (1978).
15. 11. D. S. Ksenzek, S. A. Petrova, S. V. Oleynik, M. V. Kolodgazhnyi and V. Z. Moskovskii, Spektrokhimiya, 13, 182 (1977); E. McAlpine, R. S. Sinclair and T. G. Truscott, J. Chem. Soc., Faraday Trans. I 74, 597 (1978).
16. 12. B. K. Sinha, A. G. Motten and K. W. Hanck, Chem.-Biol. Interact. 43, 371 (1983); A. J. Carmichael and P. Riesz, Arch. Biochem. Biophys. 237, 433 (1985); K. Reszka, P. Kolodziejczyk, P. G. Tsoungas and J. W. Lown, Photochem. Photobiol. 47, 625 (1988); P. M. Cullis, J. D. McClymont and M. C. R. Symons, J. Chem. Soc., Faraday Trans. 86, 591 (1990).
17. 12. B. K. Sinha, A. G. Motten and K. W. Hanck, Chem.-Biol. Interact. 43, 371 (1983); A. J. Carmichael and P. Riesz, Arch. Biochem. Biophys. 237, 433 (1985); K. Reszka, P. Kolodziejczyk, P. G. Tsoungas and J. W. Lown, Photochem. Photobiol. 47, 625 (1988); P. M. Cullis, J. D. McClymont and M. C. R. Symons, J. Chem. Soc., Faraday Trans. 86, 591 (1990).
18. 12. B. K. Sinha, A. G. Motten and K. W. Hanck, Chem.-Biol. Interact. 43, 371 (1983); A. J. Carmichael and P. Riesz, Arch. Biochem. Biophys. 237, 433 (1985); K. Reszka, P. Kolodziejczyk, P. G. Tsoungas and J. W. Lown, Photochem. Photobiol. 47, 625 (1988); P. M. Cullis, J. D. McClymont and M. C. R. Symons, J. Chem. Soc., Faraday Trans. 86, 591 (1990).
19. 12. B. K. Sinha, A. G. Motten and K. W. Hanck, Chem.-Biol. Interact. 43, 371 (1983); A. J. Carmichael and P. Riesz, Arch. Biochem. Biophys. 237, 433 (1985); K. Reszka, P. Kolodziejczyk, P. G. Tsoungas and J. W. Lown, Photochem. Photobiol. 47, 625 (1988); P. M. Cullis, J. D. McClymont and M. C. R. Symons, J. Chem. Soc., Faraday Trans. 86, 591 (1990).
20. 13. J. Eloranta, V. Vatanen, R. Mäkelä, M. Vuolle, A. Grönroos and H. Heikkilä, Magn. Reson. Chem. 34, 298 (1996).
21. 14. V. Vatanen and J. A. Pedersen, J. Chem. Soc., Perkin Trans. 2 2207 (1996).
22. 15. V. Vatanen, Licentiate Thesis, University of Jyväskylä (1995).
23. 16. D. T. Sawyer and J. L. Roberts, Jr, Experimental Electrochemistry for Chemists, pp. 204-207. Wiley, New York (1974).
24. 17. H. Larsen, S. U. Pedersen, J. A. Pedersen and H. Lund, J. Electroanal. Chem. 331, 971 (1992).
25. 18. T. Lund and S. U. Pedersen, J. Electroanal. Chem. 362, 109 (1993).
26. 19. K. Nozaki, A. Naito, T.-I. Ho, H. Hatano and S. Okazaki, J. Phys. Chem. 93, 8304 (1989).
27. 20. J. Eloranta, http://epr.chem.jyu.fi/xemr (1/9/99).
28. 21. B. Kirste, Anal. Chim. Acta 265, 191 (1992).
29. 22. J. Eloranta and M. Vuolle, Magn. Reson. Chem. 36, 98 (1998).
30. 23. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. A. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Allaham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Anders, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. J. P. Stewart, M. Head-Gordon, C. Gonzales and J. A. Pople, Gaussian 94, Revision B.3. Gaussian, Pittsburgh, PA (1995).
31. 24. D. Becke, J. Chem. Phys. 98, 5648 (1993); S. H. Vosko, L. Wilk and M. Nusair, Can. J. Phys. 58, 1200 (1980); C. Lee, W. Yang and R. G. Parr, Phys. Rev. B 37, 785 (1988).
32. 24. D. Becke, J. Chem. Phys. 98, 5648 (1993); S. H. Vosko, L. Wilk and M. Nusair, Can. J. Phys. 58, 1200 (1980); C. Lee, W. Yang and R. G. Parr, Phys. Rev. B 37, 785 (1988).
33. 24. D. Becke, J. Chem. Phys. 98, 5648 (1993); S. H. Vosko, L. Wilk and M. Nusair, Can. J. Phys. 58, 1200 (1980); C. Lee, W. Yang and R. G. Parr, Phys. Rev. B 37, 785 (1988).
34. 25. R. McWeeny, Methods of Molecular Quantum Mechanics, 2nd ed. Academic Press, London (1992); V. Barone, in Recent Advances in Density Functional Methods (Part 1). Chap. 9, edited D. P. Chong, World Scientific, Singapore, (1995).
35. 25. R. McWeeny, Methods of Molecular Quantum Mechanics, 2nd ed. Academic Press, London (1992); V. Barone, in Recent Advances in Density Functional Methods (Part 1). Chap. 9, edited D. P. Chong, World Scientific, Singapore, (1995).
36. 26. G. Schaftenaar, MOLDEN 3.4. CAOS/CAMM Center, Netherlands (1999).
37. 27. V. Barone, Chem. Phys. Lett. 262, 201 (1996); C. Gonzalez, A. Restrepo-Cossio, M. Márquez and K. B. Wiberg, J. Am. Chem. Soc. 118(23), 5408 (1996); J. B. Foresman and Æ Frisch, Exploring Chemistry with Electronic Structure Methods, 2nd ed. Gaussian, I Pittsburgh, PA (1996); J. B. Foresman, T. A. Keith, K. B. Wiberg, J. Snoonian and M. J. Frisch, J. Phys. Chem. 100, 16098 (1996).
38. 27. V. Barone, Chem. Phys. Lett. 262, 201 (1996); C. Gonzalez, A. Restrepo-Cossio, M. Márquez and K. B. Wiberg, J. Am. Chem. Soc. 118(23), 5408 (1996); J. B. Foresman and Æ Frisch, Exploring Chemistry with Electronic Structure Methods, 2nd ed. Gaussian, I Pittsburgh, PA (1996); J. B. Foresman, T. A. Keith, K. B. Wiberg, J. Snoonian and M. J. Frisch, J. Phys. Chem. 100, 16098 (1996).
39. 27. V. Barone, Chem. Phys. Lett. 262, 201 (1996); C. Gonzalez, A. Restrepo-Cossio, M. Márquez and K. B. Wiberg, J. Am. Chem. Soc. 118(23), 5408 (1996); J. B. Foresman and Æ Frisch, Exploring Chemistry with Electronic Structure Methods, 2nd ed. Gaussian, I Pittsburgh, PA (1996); J. B. Foresman, T. A. Keith, K. B. Wiberg, J. Snoonian and M. J. Frisch, J. Phys. Chem. 100, 16098 (1996).
40. 27. V. Barone, Chem. Phys. Lett. 262, 201 (1996); C. Gonzalez, A. Restrepo-Cossio, M. Márquez and K. B. Wiberg, J. Am. Chem. Soc. 118(23), 5408 (1996); J. B. Foresman and Æ Frisch, Exploring Chemistry with Electronic Structure Methods, 2nd ed. Gaussian, I Pittsburgh, PA (1996); J. B. Foresman, T. A. Keith, K. B. Wiberg, J. Snoonian and M. J. Frisch, J. Phys. Chem. 100, 16098 (1996).
41. 28. J. A. Pedersen, personal communication.
42. 29. P. Mohandas and S. Umapathy. J. Phys. Chem. A 101, 4449 (1997).
43. 30. R. Mäkelä and M. Vuolle, J. Chem. Soc., Faraday Trans. 86, 2569 (1990); R. Mäkelä and M. Vuolle, J. Chem. Soc., Faraday Trans. 1 85, 4011 (1989); R. Mäkelä and M. Vuolle, Magn. Reson. Chem. 30, 987 (1992); J. A. Pedersen and R. H. Thomson, J. Magn. Reson. 43, 373, (1981); M. B. Hocking and S. M. Mattar, J. Magn. Reson. 47, 187 (1982).
44. 30. R. Mäkelä and M. Vuolle, J. Chem. Soc., Faraday Trans. 86, 2569 (1990); R. Mäkelä and M. Vuolle, J. Chem. Soc., Faraday Trans. 1 85, 4011 (1989); R. Mäkelä and M. Vuolle, Magn. Reson. Chem. 30, 987 (1992); J. A. Pedersen and R. H. Thomson, J. Magn. Reson. 43, 373, (1981); M. B. Hocking and S. M. Mattar, J. Magn. Reson. 47, 187 (1982).
45. 30. R. Mäkelä and M. Vuolle, J. Chem. Soc., Faraday Trans. 86, 2569 (1990); R. Mäkelä and M. Vuolle, J. Chem. Soc., Faraday Trans. 1 85, 4011 (1989); R. Mäkelä and M. Vuolle, Magn. Reson. Chem. 30, 987 (1992); J. A. Pedersen and R. H. Thomson, J. Magn. Reson. 43, 373, (1981); M. B. Hocking and S. M. Mattar, J. Magn. Reson. 47, 187 (1982).
46. 30. R. Mäkelä and M. Vuolle, J. Chem. Soc., Faraday Trans. 86, 2569 (1990); R. Mäkelä and M. Vuolle, J. Chem. Soc., Faraday Trans. 1 85, 4011 (1989); R. Mäkelä and M. Vuolle, Magn. Reson. Chem. 30, 987 (1992); J. A. Pedersen and R. H. Thomson, J. Magn. Reson. 43, 373, (1981); M. B. Hocking and S. M. Mattar, J. Magn. Reson. 47, 187 (1982).
47. 30. R. Mäkelä and M. Vuolle, J. Chem. Soc., Faraday Trans. 86, 2569 (1990); R. Mäkelä and M. Vuolle, J. Chem. Soc., Faraday Trans. 1 85, 4011 (1989); R. Mäkelä and M. Vuolle, Magn. Reson. Chem. 30, 987 (1992); J. A. Pedersen and R. H. Thomson, J. Magn. Reson. 43, 373, (1981); M. B. Hocking and S. M. Mattar, J. Magn. Reson. 47, 187 (1982).
48. 31. J. Gendell, W. R. Miller, Jr and G. K. Fraenkel, J. Am. Chem. Soc. 91, 4369 (1969).
49. 32. J. A. Pedersen, J. Chem. Soc., Faraday Trans. 88, 3423 (1992).
50. 33. D. M. Holton and D. Murphy, J. Chem. Soc.. Faraday Trans, I 78, 1223 (1982).
51. 34. H. B. Stegmann, T. Jülien, K. Krohn and A. Eickhoff, Magn. Reson. Chem. 29, 178 (1991).
52. 35. P. E. Hansen, A. Kolonicny and A. Lycka, Magn. Reson. Chem. 30, 786 (1992).
53. 36. M. C. Depew and J. K. S. Wan, in The Chemistry of Quinoid Compounds, edited by S. Patai and Z. Rappoport, Vol. II. Chap. 16, Wiley, Chichester (1988).
54. 37. N. J. Flint and B. J. Tabner, J. Chem. Soc., Faraday Trans, I 83, 167 (1987).
55. 38. J. Eloranta, V. Vatanen, K. Vaskonen, R. Suontamo and M. Vuolle, J. Mol. Struct. (THEOCHEM) 424, 24 (1998).
56. 39. K. Sasaki, T. Kashimura, M. Ohura, Y. Ohsaki and N. Ohta, J. Electrochem. Soc. 137(8), 2437 (1990).
57. 40. K. Komaguchi, Y. Hatsusegawa, A. Kitani and K. Sasaki, Bull. Chem. Soc. Jpn. 64, 2686 (1991).
58. 41. D. Lunney, J. Bailes and J. D. Memory, J. Chem. Phys. 53, 3387 (1970).
59. 42. X. J. Tan, H. L. Jiang, W. L. Zhu, K. X. Chen and R. Y. Ji, J. Chem. Soc., Perkin Trans. 2 107 (1999).
60. 43. M. Sprik, J. Hutter and M. Parrinello, J. Chem. Phys. 105, 1132 (1996).