Improved Yukawa-Tsuno equation and the substitu effect on pyridine basicity

Journal of Physical Organic Chemistry

Volumn 11, Issue 7, 1998, Pages 495-503

  Reis, João Carlos R ^a   Segurado, Manuel A P ^b   Gomes De Oliveira, Jaime D ^c  

^a UNIVERSITY OF LISBON   (Portugal)

^b RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

^c INSTITUTO SUPERIOR DE ENGENHARIA DE LISBOA   (Portugal)

Author keywords

Pyridine basicity; Resonance demand; Substituent effect; Yukawa Tsuno equation

Indexed keywords

EID: 0001735903     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-1395(199807)11:7<495::aid-poc28>3.0.co;2-k     Document Type: Article

References (59)

1. Y. Yukawa and Y. Tsuno. Bull. Chem. Soc. Jpn. 32, 965-971 (1959).
2. Y. Yukawa and Y. Tsuno. Bull. Chem. Soc. Jpn. 32, 971-981 (1959).
3. M. Ludwig, S. Wold and O. Exner. Acta Chem. Scand. 46, 549-554 (1992).
4. O. Exner. Correlation Analysis of Chemical Data. Plenum Press, New York (1988).
5. J. Shorter. Correlation Analysis of Organic Reactivity. Wiley, Chichester (1982).
6. O. Pytela. Collect. Czech. Chem. Commun. 60, 1502-1528 (1995).
7. O. Pytela. Collect. Czech. Chem. Commun. 61, 704-712 (1996).
8. O. Pytela. Collect. Czech. Chem. Commun. 61, 1191-1204 (1996).
9. J. C. R. Reis, M. A. P. Segurado and J. D. G. de Oliveira. J. Phys. Org. Chem. 8, 5-14 (1995).
10. M. Sjöström and S. Wold. Chem. Scr. 9, 200-210 (1976).
11. J. C. R. Reis, M. A. P. Segurado and J. D. G. de Oliveira. J. Phys. Org. Chem. 8, 671-688 (1995).
12. M. J. S. Dewar, R. Golden and J. M. Harris. J. Am. Chem. Soc. 93, 4187-4195 (1971).
13. M. Sawada, M. Ichihara, I. Yukawa, T. Nakachi and Y. Tsuno. Bull. Chem. Soc. Jpn. 53, 2055-2060 (1980).
14. J. S. Alper and R. I. Gelb. J. Phys. Chem. 90, 4747-4751 (1990).
15. A. J. Hoefnagel, M. A. Hoefnagel and B. M. Wepster. J. Org. Chem. 43, 4720-4745 (1978).
16. A. J. Hoefnagel and B. M. Wepster. J. Chem. Soc., Perlon Trans. 2 977-986 (1989).
17. Y. Yukawa, Y. Tsuno and M. Sawada. Bull. Chem. Soc. Jpn. 39, 2274-2286 (1966).
18. J. Hine. J. Am. Chem. Soc. 81, 1126-1129 (1959).
19. H. H. Jaffé. J. Am. Chem. Soc. 81, 3020-3021 (1959).
20. R. A. Day, Jr. and A. L. Underwood. J. Chem. Educ. 72, 596-598 (1995).
21. J. Shorter. Pure Appl. Chem. 66, 2451-2468 (1994).
22. R. Luus and T. H. I. Jaakola. AIChE J. 19, 760-766 (1973).
23. O. Exner. Collect. Czech. Chem. Commun. 31, 3222-3251 (1966).
24. O. Exner. Collect. Czech. Chem. Commun. 40, 2781-2791 (1975).
25. S. Ehrenson. J. Org. Chem. 44, 1793-1797 (1979).
26. K. Clarke and K. Rothwell. J. Chem. Soc. 1885-1895 (1960).
27. A. Bryson. J. Am. Chem. Soc. 82, 4871-4877 (1960).
28. G. Butt, R. D. Topsom and R. W. Taft. J. Mol. Struct. 153, 141-146 (1987).
29. M. Taagepera, K. D. Summerhays, W. J. Hehre, R. D. Topsom, A. Pross, L. Radom and R. W. Taft. J. Org. Chem. 46, 891-903 (1981).
30. T. J. Broxton, G. Butt, R. Liu, L. H. Teo, R. D. Topsom and A. R. Katritzky. J. Chem. Soc., Perkin Trans. 2 463-466 (1974).
31. H. H. Jaffé and G. O. Doak. J. Am. Chem. Soc. 77, 4441-4444 (1955).
32. S. Ehrenson, R. T. C. Brownlee and R. W. Taft. Prog. Phys. Org. Chem. 10, 1-80 (1973).
33. G. B. Ellam and C. D. Johnson. J. Org. Chem. 36, 2284-2288 (1971).
34. R. T. C. Brownlee and R. D. Topsom. Tetrahedron Lett. 5187-5190 (1972).
35. R. W. Taft and C. A. Grob. J. Am. Chem. Soc. 96, 1236-1238 (1974).
36. C. D. Johnson, I. Roberts and P. G. Taylor. J. Chem. Soc., Chem. Commun. 897-899 (1977).
37. M. Charton. J. Org. Chem. 44, 2097-2099 (1979).
38. C. D. Johnson, I. Roberts and P. G. Taylor. J. Chem. Soc., Perkin Trans. 2 409-413 (1981).
39. W. R. Reynolds, P. Dais, D. W. Maclntyre, R. D. Topsom, S. Marriott, E. von Nagy-Felsobuki and R. W. Taft. J. Am. Chem. Soc. 105, 378-384 (1983).
40. H. C. Brown and X. R. Mihm. J. Am. Chem. Soc. 77, 1723-1726 (1955).
41. J. B. Lambert and R. A. Singer. J. Am. Chem. Soc. 114, 10246-10248 (1992).
42. Y. R. Luo and J. L. Holmes. J. Phys. Org. Chem. 7, 403-411 (1994).
43. J.-L. M. Abboud, J. Catalán, J. Elguero and R. W. Taft. J. Org. Chem. 53, 1137-1140 (1988).
44. D. H. Aue, H. M. Webb, W. R. Davidson, P. Toure, H. P. Hopkins, Jr, S. P. Moulik and D. V. Jahagirdar. J. Am. Chem. Soc. 113, 1770-1780 (1991).
45. O. Exner and S. Böhm. J. Chem. Soc., Perkin Trans. 2 1235-1240 (1997).
46. A. J. Hoefnagel, M. A. Hoefnagel and B. M. Wepster. J. Am. Chem. Soc. 98, 6194-6197 (1976).
47. M. Fujio, K. Nakata, Y. Tsuji, T. Otsu and Y. Tsuno. Tetrahedron Lett. 33, 321-324 (1992).
48. K. Nakata, M. Fujio, Y. Saeki, M, Mishima, Y. Tsuno and K. Nishimoto, J. Phys. Org. Chem. 9, 573-582 (1996).
49. R. A. Jones and A. R. Katritzky. J. Chem. Soc. 1317-1323 (1959).
50. K. Nakata, M. Fujio, Y. Saeki, M. Mishima, Y. Tsuno and K. Nishimoto. J. Phys. Org. Chem. 9, 561-572 (1996).
51. Y. Tsuno and M. Fujio. Chem. Soc. Rev. 25, 129-139 (1996).
52. M. Decouzon, P. Ertl, O. Exner, J.-F. Gal and P.-C. Maria. J. Am. Chem. Soc. 115, 12071-12078 (1993).
53. J. Gerratt, D. L. Cooper, P. B. Karadakov and M. Raimondi. Chem. Soc. Rev. 26, 87-100 (1997).
54. R. Notario, M. Herreros, A. El-Hammadi, H. Homan, J.-L. M. Abboud, I. Forfar, R. M. Claramunt and J. Elguero. J. Phys. Org. Chem. 7, 657-662 (1994).
55. M. Fujio, T. Miyamoto, Y. Tsuji and Y. Tsuno. Tetrahedron Lett. 32, 2929-2932 (1991).
56. Y. Tsuno, M. Fujio and Y. Yukawa. Bull. Chem. Soc. Jpn. 48, 3324-3329 (1975).
57. R. W. Taft and R. D. Topsom. Prog. Phys. Org. Chem. 16, 1-83 (1987).
58. J. S. Alper and R. I. Gelb. J. Phys. Chem. 95, 104-108 (1991).
59. R. M. C. Gonçalves, F. E. L. Martins and R. A. E. Leitão. J. Phys. Chem. 98, 9537-9540 (1994).