Regioselectivity on the cooxidation of 5,6-dihydroxyindole and its 2-carboxy derivative from the quantum chemical calculations

Chemical Physics Letters

Volumn 490, Issue 4-6, 2010, Pages 226-229

  Okuda, Hidekazu ^a   Wakamatsu, Kazumasa ^b   Ito, Shosuke ^b   Sota, Takayuki ^a  

^a WASEDA UNIVERSITY   (Japan)

^b FUJITA HEALTH UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CO OXIDATION; CONTROLLED REACTIONS; DIHYDROXYINDOLE; ELECTRON TRANSFER; EUMELANINS; HETERODIMERIZATION; QUANTUM CHEMICAL CALCULATIONS; REACTIVITY INDICATORS; THEORETICAL PREDICTION;

QUANTUM CHEMISTRY;

INDICATORS (CHEMICAL);

EID: 77950863853     PISSN: 00092614     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cplett.2010.03.054     Document Type: Article

References (42)

1. Ito S. Pigment Cell Res. 16 (2003) 230
2. d'Ischia M., Napolitano A., Pezzella A., Land E.J., Ramsden C.A., and Riley P.A. Adv. Heterocycl. Chem. 89 (2005) 1
3. Meredith P., Powell B.J., Riesz J., Nighswander-Rempel S.P., Pederson M.R., and Moore E.G. Soft Matter 2 (2006) 37
4. Meredith P., and Sarna T. Pigment Cell Res. 19 (2006) 572
5. Ito S., and Wakamatsu K. Photochem. Photobiol. 84 (2008) 582
6. Simon J.D., Hong L., and Peles D.N. J. Phys. Chem. B 112 (2008) 13201
7. Simon J.D., Peles D., Wakamatsu K., and Ito S. Pigment Cell Melanoma Res. 22 (2009) 563
8. d'Ischia M., Napolitano A., Pezzella A., Meredith P., and Sarna T. Angew. Chem. Int. Ed. 48 (2009) 3914
9. Napolitano A., Corradini M.G., and Prota G. Tetrahedron Lett. 26 (1985) 2805
10. d'Ischia M., Napolitano A., Tsiakas K., and Prota G. Tetrahedron 46 (1990) 5789
11. Napolitano A., Crescenzi O., and Prota G. Tetrahedron Lett. 34 (1993) 885
12. Pezzella A., Napolitano A., d'Ischia M., and Prota G. Tetrahedron 52 (1996) 7913
13. Pezzella A., Vogna D., and Prota G. Tetrahedron 58 (2002) 3681
14. Pezzella A., Vogna D., and Prota G. Tetrahedron: Asymmetry 14 (2003) 1133
15. Panzella L., Pezzella A., Napolitano A., and d'Ischia M. Org. Lett. 9 (2007) 1411
16. Pezzella A., Panzella L., Natangelo A., Arzillo M., Napolitano A., and d'Ischia M. J. Org. Chem. 72 (2007) 9225
17. Il'ichev Y.V., and Simon J.D. J. Phys. Chem. B 107 (2003) 7162
18. Powell B.J., Baruah T., Bernstein N., Brake K., McKenzie R.H., Meredith P., and Pederson M.R. J. Chem. Phys. 120 (2004) 8608
19. Powell B.J. Chem. Phys. Lett. 402 (2005) 111
20. Okuda H., Nakamura A., Wakamatsu K., Ito S., and Sota T. Chem. Phys. Lett. 433 (2007) 355
21. Tran M.L., Powell B.J., and Meredith P. Biophys. J. 90 (2006) 743
22. Kaxiras E., Tsolakidis A., Zonios G., and Meng S. Phys. Rev. Lett. 97 (2006) 218102
23. Pezzella A., et al. J. Am. Chem. Soc. 128 (2006) 15490
24. Meng S., and Kaxiras E. Biophys. J. 94 (2008) 2095
25. Meng S., and Kaxiras E. Biophys. J. 95 (2008) 4396
26. d'Ischia M., Crescenzi O., Pezzella A., Arzillo M., Panzella L., Napolitano A., and Barone V. Photochem. Photobiol. 84 (2008) 600
27. Okuda H., Wakamatsu K., Ito S., and Sota T. J. Phys. Chem. A 112 (2008) 11213
28. Pezzella A., et al. J. Org. Chem. 74 (2009) 3727
29. Anderson J.S.M., Melin J., and Ayers P.W. J. Chem. Theory Comput. 3 (2007) 358
30. Anderson J.S.M., Melin J., and Ayers P.W. J. Chem. Theory Comput. 3 (2007) 375
31. Parr R.G., and Yang W. Density-Functional Theory of Atoms and Molecules (1989), Oxford University Press, New York
32. Koch W., and Holthausen M.C. A Chemist's Guide to Density Functional Theory. second edn. (2001), Wiley-VCH, Weinheim
33. Becke A.D. J. Chem. Phys. 98 (1993) 5648
34. Petersson G.A., Bennett A., Tensfeldt T.G., Al-Laham M.A., Shirley W.A., and Mantzaris J. J. Chem. Phys. 89 (1988) 2193
35. Clark T., Chandrasekhar J., Spitznagel G.W., and Schleyer P.V.R. J. Comput. Chem. 4 (1983) 294
36. Cammi R., Mennucci B., and Tomasi J. J. Phys. Chem. A 104 (2000) 5631
37. Breneman C.M., and Wiberg K.B. J. Comput. Chem. 11 (1990) 361
38. Runge E., and Gross E.K.U. Phys. Rev. Lett. 52 (1984) 997
39. M.J. Frisch et al., Gaussian03, Revision D.02, Gaussian Inc., Wallingford CT, 2004.
40. Charkoudian L.K., and Franz K.J. Inorg. Chem. 45 (2006) 3657
41. Olsen S., et al. J. Am. Chem. Soc. 129 (2007) 6672
42. Orio M., Pantazis D.A., and Neese F. Photosynth. Res. 102 (2009) 443