Thermosolvatochromism of merocyanine polarity indicators in pure and aqueous solvents: Relevance of solvent lipophilicity

Journal of Organic Chemistry

Volumn 71, Issue 24, 2006, Pages 9068-9079

  Martins, Clarissa T ^a   Lima, Michelle S ^a   El Seoud, Omar A ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL MODIFICATION; ORGANIC SOLVENTS; SOLUBILITY; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

APROTIC SOLVENTS; AQUEOUS SOLVENTS; SOLVATOCHROMISM;

DYES;

ACETONITRILE; ALKYL GROUP; BROMINE DERIVATIVE; DIMETHYL SULFOXIDE; HYDROGEN; MEROCYANINE; METHANOL; PHENOL DERIVATIVE; PROPANOL; PYRIDINIUM DERIVATIVE; SOLVENT; WATER;

ALKALINITY; AQUEOUS SOLUTION; ARTICLE; DIPOLE; HEAT TREATMENT; HYDRATION; HYDROGEN BOND; HYDROPHOBICITY; LIPOPHILICITY; SOLVATION; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 33845215914     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061533e     Document Type: Article

References (68)

1. Tada, E. B.; Novaki, L. P.; El Seoud, O. A. J. Phys. Org. Chem. 2000, 13, 679-687.
2. Antonious, M. S.; Tada, E. B.; El Seoud, O. A. J. Phys. Org. Chem. 2002, 15, 403-412.
3. Tada, E. B.; Silva, P. L.; El Seoud, O. A. J. Phys. Org. Chem. 2003, 16, 691-699.
4. Tada, E. B.; Silva, P. L.; El Seoud, O. A. Phys. Chem. Chem. Phys. 2003, 5, 5378-5385.
5. Tada, E. B.; Silva, P. L.; Tavares, C.; El Seoud, O. A. J. Phys. Org. Chem. 2005, 18, 398-407.
6. Leo, A. J.; Hansch, C. Perspect. Drug Discovery Des. 1999, 17, 1-25.
7. Reichardt, C. In Solvents and Solvent Effects in Organic Chemistry, 3rd ed.; VCH: Weinheim, 2003; p 389.
8. Siviero, F.; El Seoud, O. A. J. Phys. Org. Chem. 2006, in press.
9. Coleman, C. A.; Murray, C. J. J. Org. Chem. 1992, 57, 3578-3582.
10. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
11. Reichardt, C. Chem. Rev. 1994, 94, 2319-2358.
12. Kamlet, M. J.; Abboud, J. L. M.; Taft, R. W. Prog. Phys. Org. Chem. 1981, 13, 485-630.
13. Abraham, M. H.; Grellier, P. L.; Abboud, J. L. M.; Doherty, R. M.; Taft, R. W. Can. J. Chem. 1988, 66, 2673-2686.
14. Laurence, C.; Nicolet, P.; Dalati, M. T.; Abboud, J. L. M.; Notario, R. J. Phys. Chem. 1994, 98, 5807-5816.
15. Kamlet, M. J.; Doherty, R. M.; Abraham, M. H.; Marcus, Y.; Taft, R. W. J. Phys. Chem. 1988, 92, 5244-5255.
16. Abraham, M. H. Chem. Soc. Rev. 1993, 22, 73-83.
17. Steyaert, G.; Lisa, G.; Gaillard, P.; Boss, G.; Reymond, F.; Girault, H. H.; Carrupt, P. A.; Testa, B. J. Chem. Soc,. Faraday Trans. 1997, 93, 401-406.
18. Novaki, L. P.; El Seoud, O. A. Ber. Bunsenges. Phys. Chem. 1996, 100, 648-655 and references cited therein.
19. Hill, T.; Lewicki, P. In Statics Methods and Applications, A Comprehensive Reference for Science, Industry and Data Mining, 1st ed.; StatSoft: Tulsa, 2006; pp 555-757.
20. Kamlet, M. J.; Taft, R. W. J. Am. Chem. Soc. 1976, 98, 377-383.
21. Krygowski, T. M.; Radomski, J. P.; Rzeszowiak, A.; Wrona, P. K.; Reichardt, C. Tetrahedron 1981, 37, 119-125.
22. El Seoud, O. A. J. Mol. Liq. 1997, 72, 85-103 and references cited therein.
23. Taft, R. W.; Abraham, M. H.; Doherty, R. M.; Kamlet, M. J. J. Am. Chem. Soc. 1985, 107, 3105-3110.
24. Meylan, W. M.; Howard, P. H. J. Pharm. Sci. 1995, 84, 83-92.
25. Suppan, P. G. N. In Solvatochromism; The Royal Society of Chemistry: Cambridge, 1997; pp 21-67 and references cited therein.
26. Marcus, Y. Chem. Soc. Rev. 1993, 22, 409-416.
27. Shulgin, I.; Ruckenstein, E. J. Phys. Chem. B 1999, 103, 872-877.
28. Marcus, Y. Monatsh. Chem. 2001, 132, 1387-1411.
29. Hefter, G.; Marcus, Y.; Waghorne, W. E. Chem. Rev 2002, 102, 2773-2835.
30. Mendes, C. L. D.; da Silva, C. O.; da Silva, E. C. J. Phys. Chem A 2006, 110, 4034-4041.
31. Rafols, C.; Roses, M.; Bosch, E. J. Chem. Soc. Perkin Trans. 1997, 2, 243-248.
32. Buhvestov, U.; Rived, F.; Rafols, C.; Bosch, E.; Roses, M. J. Phys. Org. Chem. 1998, 11, 185-192.
33. Barlin, G. B.; Perrin, D. D. Quart. Rev. 1966, 20, 75-&.
34. Kingston, B.; Symons, M. C. R. J. Chem. Soc., Faraday Trans. 1973, 2, 69, 978-992.
35. Symons, M. C. R. Pure Appl. Chem. 1986, 58, 1121-1132.
36. Gopalakrishnan, G.; Hogg, J. L. J. Org. Chem. 1984, 49, 3161-3166.
37. Shin, D. N.; Wijnen, J. W.; Engberts, J. B. F. N.; Wakisaka, A. J. Phys. Chem. B 2001, 105, 6759-6762.
38. Borin, I. A.; Skaf, M. S. J. Chem. Phys. 1999, 110, 6412-6420.
39. Mizuno, K.; Imafuji, S.; Ochi, T.; Ohta, T.; Maeda, S. J. Phys. Chem. B 2000, 104, 11001-11005.
40. Shashkov, S. N.; Kiselev, M. A.; Tioutiounnikov, S. N.; Kiselev, A. M.; Lesieur, P. Physica B 1999, 271, 184-191.
41. Cabral, J. T.; Luzar, A.; Teixeira, J.; Bellissent-Funel, M. C. J. Chem. Phys. 2000, 113, 8736-8745.
42. Catalan, J.; Diaz, C.; Garcia-Blanco, F. J. Org. Chem. 2001, 66, 5846-5852.
43. Zana, R.; Eliebari, M. J. J. Phys. Chem. 1993, 97, 11134-11136.
44. Haak, J. R.; Engberts, J. B. F. N. Rec. Trav. Chim. 1986, 105, 307-311.
45. Harris, K. R.; Newitt, P. J. J. Chem. A 1999, 103, 6508-6513.
46. Nishikawa, K.; Hayashi, H.; Iijima, T. J. Phys. Chem. 1989, 93, 6559-6565.
47. Huelsekopf, M.; Ludwig. R. J. Mol. Liq. 2000, 85, 105-125.
48. Shulgin, I.; Ruckenstein, E. J. Phys. Chem. B 1999, 103, 2496-2503.
49. Kemp, D. S.; Paul, K. G. J. Am. Chem. Soc. 1975, 97, 7305-7312.
50. Grate, J. W.; Mcgill, R. A.; Hilvert, D. J. Am. Chem. Soc. 1993, 115, 8577-8584.
51. Catalan, J.; Diaz, C.; Garcia-Blanco, F. J. Org. Chem. 2000, 65, 3409-3415.
52. Huskey, W. P.; Warren, C. T.; Hogg, J. L. J. Org. Chem. 1981, 46, 59-63.
53. Gopalakrishnan, G.; Hogg, J. L. J. Org. Chem. 1984, 49, 3161-3166.
54. Neuvonen, H. J. Chem. Soc., Perkin Trans. 1987, 2, 159-167.
55. Mata-Segreda, J. F. J. Am. Chem. Soc. 1988, 110, 6224-6230.
56. Galema, S. A.; Blandamer, M. J.; Engberts, J. B. F. N. J. Org. Chem. 1989, 54, 1227-1229.
57. Mousa, M. A.; Diefallah, E. H. M.; Dessouki, H. A.; Atwa, S. T. Thermochim. Acta 1989, 141, 1-8.
58. El Seoud, O. A.; El Seoud, M. I.; Parah, J. P. S. J. Org. Chem. 1997, 62, 5928-5933.
59. Tian, J. H.; Tan, J.; Schowen, K. B.; Schowen, R. L. Can. J. Chem. 1999, 77, 781-786.
60. Venkatasubban, K. S.; Bush, M.; Ross, E.; Schultz, M.; Garza, O. J. Org. Chem. 1998, 63, 6115-6118.
61. Sorensen, P. E. Acta Chem. Scand. A 1976, 30, 673-679.
62. Henderson, J. W.; Haake, P. J. Org. Chem. 1977, 42, 3989-3994.
63. Davidson, S. J.; Jencks, W. P. J. Am. Chem. Soc. 1969, 91, 225-234.
64. Brooker, L. G. S.; Keyes, G. H.; Heseltine, D. W. J. Am. Chem. Soc. 1951, 73, 5350-5356.
65. Minch, M. J.; Shah, S. S. J. Chem. Educ. 1977, 54, 709.
66. Minch, M. J.; Shah, S. S. J. Org. Chem. 1979, 44, 3252-3255.
67. Martins, C. T.; Lima, M. S.; El Seoud, O. A. J. Phys. Org. Chem. 2005, 18, 1072-1085.
68. Anslyn, E. V.; Dougherty, D. A. In Modern Physical Organic Chemistry; University Science Books: Sausalito, 2004; p 259.