Differentiating between dipolarity and polarizability effects of solvents using the solvatochromism of barbiturate dyes

European Journal of Organic Chemistry

Volumn , Issue 26, 2008, Pages 4475-4481

  Bauer, Mirko ^a   Rollberg, Anja ^a   Barth, Anina ^a   Spange, Stefan ^a  

^a CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Barbiturates; Donor acceptor systems; Polarity; Polyenes; Solvatochromism; Solvent effects

Indexed keywords

EID: 53849098405     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800355     Document Type: Article

References (62)

1. a) C. Reichardt, Chem. Rev. 1994, 94, 2319-2358;
2. b) P. Suppan, N. Ghoneim, Solvatochromism, The Royal Society of Chemistry, London, 1997;
3. c) C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 3rd ed., Wiley-VCH, Weinheim, 2003.
4. P. Müller, Pure Appl. Chem. 1994, 66, 1151.
5. C. Chiappe, D. Pieraccini, J. Phys. Org. Chem. 2005, 18, 275-297.
6. A. Oehlke, K. Hofmann, S. Spange, New J. Chem. 2006, 30, 533-536.
7. a) S. Spange, A. Reuter, E. Vilsmeier, Colloid Polym. Sci. 1996, 274, 59-69;
8. b) S. Spange, A. Reuter, Langmuir 1999, 15, 141-150;
9. c) S. Spange, A. Reuter, D. Lubda, Langmuir 1999, 15, 2103-2111;
10. d) S. Spange, Y. Zimmermann, A. Gräser, Chem. Mater. 1999, 11, 3245-3251;
11. e) S. Spange, E. Vilsmeier, Y. Zimmermann, J. Phys. Chem. B 2000, 104, 6417-6428.
12. a) R. S. Helburn, S. C. Rutan, J. Pompano, D. Mitchern, W. T. Patterson, Anal. Chem. 1994, 66, 610-618;
13. b) S. C. Rutan, J. M. Harris, J. Chromatogr. A 1993, 656, 197-215.
14. R. W. Sinkeldam, Y. Tor, Org. Biomol. Chem. 2007, 5, 2523-2528.
15. F. Jara, C. Mascayano, M. C. Rezende, C. Tirapegui, A. Urzua, J. Inclusion Phenom. Macrocycl. Chem. 2006, 54, 95-99.
16. S. Spange, C. Schmidt, H. R. Kricheldorf, Langmuir 2001, 17, 856-865.
17. L. P. Novaki, O. A. El Seoud, Ber. Bunsen-Ges. Phys. Chem. 1996, 100, 648-655.
18. a) R. W. Taft, M. J. Kamlet, J. Chem. Soc. Perkin Trans. 2 1979, 1723-1727;
19. b) M. J. Kamlet, T. H. Hall, J. Bodkin, R. W. Taft, J. Org. Chem. 1979, 44, 2599-2604;
20. c) M. J. Kamlet, J.-L. M. Abboud, M. H. Abraham, R. W. Taft, J. Org. Chem. 1983, 48, 2877-2887.
21. δ has only three values: 1.0 for aromatic, 0.5 for polyhalogenated and 0.0 for aliphatic solvents.
22. a) J. Catalán, V. López, P. Pérez, R. Martín-Villamil, J.-G. Rodriguez, Liebigs Ann. 1995, 241-252;
23. b) J. Catalán, V. López, P. Pérez, Liebigs Ann. 1995, 793-795;
24. c) J. Catalán, C. Díaz, V. López, P. Pérez, J.-L. G. DePaz, J.-G. Rodriguez, Liebigs Ann. 1996, 1785-1794;
25. d) J. Catalán, C. Díaz, Liebigs Ann./Recueil 1997, 1941-1949;
26. e) J. Catalán, C. Díaz, Eur. J. Org. Chem. 1999, 885-891.
27. J. Catalán, H. Hopf, Eur. J. Org. Chem. 2004, 4694-4702.
28. G. Sun, Y.-Q. Qiu, H. Z. Sun, Z.-M. Su, J.-D. Feng, Y. L. Zhu, Chin. J. Chem. 2004, 22, 425-429.
29. X. Zhou, A.-M. Ren, J. K. Feng, X. J. Liu, C. C. Shu, Chin. J. Chem. 2004, 22, 38-46.
30. a) R. Andreu, M. A. Cerdan, J. Orduna, ARKIVOC 2004, 32-41;
31. b) R. Andreu, M. J. Blesa, L. Carrasquer, J. Garín, J. Orduna, B. Villacampa, R. Alcalá, J. Casado, M. C. Ruiz Delgado, J. T. López Navarrete, M. Allain, J. Am. Chem. Soc. 2005, 127, 8835-8845.
32. G. Bourhill, J.-L. Brédas, L.-T. Cheng, S. R. Marder, F. Meyers, J. W. Perry, B. G. Tiemann, J. Am. Chem. Soc. 1994, 116, 2619-2620.
33. M. Blanchard-Desce, V. Alain, P. V. Bedworth, S. R. Marder, A. Fort, C. Runser, M. Barzoukas, S. Lebus, R. Wortmann, Chem. Eur. J. 1997, 3, 1091-1104.
34. A. V. Kulinich, N. A. Derevyanko, A. A. Ishchenko, Russ. J. Gen. Chem. (Engl. Trans.) 2006, 76, 1441-1457.
35. a) M. C. Rezende, P. Campodonico, E. Abuin, J. Kossanyi, Spectrochim. Acta Part A 2001, 57, 1183-1190;
36. b) M. C. Rezende, P. Flores, J. Guerrero, L. Villarroel, Spectrochim. Acta Part A 2004, 60, 1637-1640.
37. S. Nakatsuji, T. Yahiro, K. Nakashima, S. Akiyama, H. Nakazumi, Chem. Express 1989, 4, 601-604.
38. G. U. Bublitz, R. Ortiz, S. R. Marder, S. G. Boxer, J. Am. Chem. Soc. 1997, 119, 3365-3376.
39. a) S. Horie, M. Nagata, J. Nakano, H. Sato, DE-3150266, 1982, Chem. Abstr. 1983, 99, 131329;
40. b) K. Inai, N. Go, H. Miyazaki, T. Miyaji, JP-03012660, 1991, Chem. Abstr. 1991, 115, 146585.
41. See selected publications: a) P. E. Blatz, J. H. Mohler, H. V. Navangul, Biochemistry 1972, 11, 848-855;
42. b) T. Baasov, M. Sheves, J. Am. Chem. Soc. 1985, 107, 7524-7533;
43. c) Y. Kawabe, H. Ikeda, T. Sakai, K. Kawasaki, J. Mater. Chem. 1992, 2, 1025-1031.
44. See selected publications: a) N. Acton, A. Brossi, D. L. Newton, M. B. Sporn, J. Med. Chem. 1980, 23, 805-809;
45. b) C. C. Willhite, M. I. Dawson, K. J. Williams, Toxicol. Appl. Pharmacol. 1984, 74, 397-410;
46. c) E. P. Jaeger, P. C. Jurs, T. R. Stouch, Eur. J. Med. Chem. 1993, 28, 275-290.
47. a) A. M. Asiri, Molecules 2000, 5, M170;
48. b) A. M. Asiri, Molecules 2000, 57, 1183-1190;
49. c) A. M. Asiri, Appl. Orgonomet. Chem. 2001, 15, 905-915.
50. M. A. Whiteley, J. Chem. Soc. Trans. 1907, 91, 1330-1350.
51. S. Naya, K. Yoda, M. Nitta, Tetrahedron 2005, 61, 8616-8624.
52. a) T. Bug, H. Mayr, J. Am. Chem. Soc. 2003, 125, 12980-12986;
53. b) H. Mayr, T. Bug, M. F. Gotta, N. Hering, B. Irrgang, B. Janker, B. Kempf, R. Loos, A. R. Ofial, G. Remennikov, H. Schimmel, J. Am. Chem. Soc. 2001, 123, 9500-9512.
54. -1, E is the electrophilicity parameter, N is the nucleophilicity parameter, and s is a nucleophile-specific slope parameter (s ≈ 1 can be assumed for such qualitative considerations).
55. K.-D. Nolte, S. Dähne, J. Prakt. Chem. 1976, 318, 643-657.
56. See, for example: a) Z. He, D. Gosztola, Y. Deng, G. Gao, M. R. Wasielewski, L. D. Kispert, J. Phys. Chem. B 2000, 104, 6668-6673;
57. b) D. Laage, P. Plaza, M. Blanchard-Desce, M. M. Martin, Photochem. Photobiol. Sci. 2002, 1, 526-535.
58. Y. Marcus, Chem. Soc. Rev. 1993, 22, 409-416.
59. J. G. Kirkwood, J. Chem. Phys. 1934, 2, 351-361.
60. a) B. W. Domagalska, K. A. Wilk, S. Wysocki, Phys. Chem. Chem. Phys. 2003, 5, 696-702;
61. b) B. W. Domagalska, K. A. Wilk, R. Zielinski, J. Photochem. Photobiol. A: Chem. 2006, 184, 193-203.
62. Origin 5.0, MicroCal Software Inc., Northampton, MA, USA, 1997.