Structure-reactivity correlations in the reaction of 2,4-dinitrophenyl X-substituted benzoates with alicyclic secondary amines

Canadian Journal of Chemistry

Volumn 77, Issue 5-6, 1999, Pages 659-666

  Um, Ik Hwan ^a   Min, Ji Sook ^a   Lee, Hye Won ^a  

^a Ewha Womans University   (South Korea)

Author keywords

Aminolysis; Br nsted type plot; Rate determining step; Structure reactivity correlations

Indexed keywords

2,4 DINITROPHENOL; ALICYCLIC AMINE; BENZOIC ACID; DIMETHYL SULFOXIDE; WATER;

ACIDITY; ARTICLE; CHEMICAL REACTION KINETICS; EQUILIBRIUM CONSTANT; REACTION ANALYSIS; SPECTROPHOTOMETRY; STRUCTURE ACTIVITY RELATION;

RATE CONSTANTS;

AMINOLYSIS; BRØNSTED-TYPE PLOT; DINITROPHENYL; MICROCONSTANTS; RATE CONSTANT K; RATE DETERMINING STEP; SECOND-ORDER RATE CONSTANTS; SECONDARY AMINES; STRUCTURE REACTIVITY; STRUCTURE–REACTIVITY CORRELATION;

AMINES;

EID: 0033306509     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v99-046     Document Type: Article

References (46)

1. W.P. Jencks. In Catalysis in chemistry and enzymology. McGraw-Hill Book Company, New York. 1969. pp. 463-554.
2. (a) D.J. Hupe, and W.P. Jencks. J. Am. Chem. Soc. 99, 451 (1977);
3. (b) W.P. Jencks, S.R. Brant, J.R. Gandler, G. Fendrich, and C. Nakamura. J. Am. Chem. Soc. 104, 7045 (1982);
4. (c) D. Stefanidis, S. Cho, S. Dhe-Paganon, and W.P. Jencks. J. Am. Chem. Soc. 115, 1650 (1993).
5. (a) H.K. Oh, S.Y. Woo, C.H. Shin, Y.S. Park, and I. Lee. J. Org. Chem. 62, 5780 (1997);
6. (b) H.J. Koh, J.W. Lee, H.W. Lee, and I. Lee. New J. Chem. 21, 447 (1997);
7. (c) H.J. Koh, S.I. Kirn, B.C. Lee, and I. Lee. J. Chem. Soc. Perkin Trans. 2, 1353 (1996);
8. (d) H.K. Oh, C.H. Shin, and I. Lee. J. Chem. Soc. Perkin Trans. 2, 1169 (1995).
9. (a) E.A. Castro, M.I. Pizzaro, and J.G. Santos. J. Org. Chem. 61, 5982 (1996);
10. (b) E.A. Castro, F. Ibanez, J.G. Santos, and C. Ureta. J. Org. Chem. 58, 4908 (1993);
11. (c) E.A. Castro, M. Cubillos, and J.G. Santos. J. Org. Chem. 61, 3501 (1996);
12. (d) E.A. Castro and C.A. Araneda. J. Org. Chem. 62, 126 (1997).
13. (a) A. Williams. Chem. Soc. Rev. 23, 93 (1994);
14. (b) S. Ba-Saif, A.K. Luthra, and A. Williams. J. Am. Chem. Soc. 111, 2647 (1989).
15. (a) D.F. DeTar. J. Am. Chem. Soc. 104, 7205 (1982);
16. (b) T. Okuyama, H. Takano, and K. Senda. Bull. Chem. Soc. Jpn. 69, 2639 (1996).
17. N.B. Chapman and J. Shorter (Editors). In Advances in linear free energy relationships. Plenum, London. 1972.
18. (a) I.H. Um, E.K. Chung, and S.M. Lee. Can. J. Chem. 76, 729 (1998);
19. (b) I.H. Um, Y.J. Hong, and D.S. Kwon. Tetrahedron, 53, 5073 (1997);
20. (c) I.H. Um, E.S. Yeom, H.J. Kwon, and D.S. Kwon. Bull. Korean Chem. Soc. 18, 865 (1997);
21. (d) I.H. Um, M.J. Kim, J.S. Min, and D.S. Kwon. Bull. Korean Chem. Soc. 18, 523 (1997);
22. (e) I.H. Um, E.K. Chung, and D.S. Kwon. Tetrahedron Lett. 38, 4787 (1997).
23. (a) F.M. Menger and J.H. Smith. J. Am. Chem. Soc. 94, 3824 (1972);
24. (b) M.J. Colthurst and A. Williams, J. Chem. Soc. Perkin Trans. 2, 1493 (1997);
25. (c) E.A. Castro and G.B. Steinfort. J. Chem. Soc. Perkin Trans. 2, 453 (1983);
26. (d) E.A. Castro and C.L. Santander. J. Org. Chem. 50, 3595 (1985);
27. (e) E.A. Castro and J.L. Valdivia. J. Org. Chem. 51, 1668 (1986);
28. (f) J.F. Kirsch and A. Kline. J. Am. Chem. Soc. 91, 1841 (1969).
29. (a) J.F. Kirsch, W. Clewell, and A. Simon. J. Org. Chem. 33, 127 (1968);
30. (b) M. Caplow and W.P. Jencks. Biochemistry, 1, 883 (1962);
31. (c) V.R. Correia, I.M. Cuccovia, and H. Chaimovich. J. Phys. Org. Chem. 4, 13 (1991).
32. R.P. Bell. In The proton in chemistry. Methuen, London. 1973. p. 159.
33. (a) W.P. Jencks and M. Gilchrist. J. Am. Chem. Soc. 90, 2622 (1968);
34. (b) E.A. Castro, M. Salas, and J.G. Santos. J. Org. Chem. 56, 4919 (1991);
35. (c) E.A. Castro and C. Ureta. J. Org. Chem. 54, 2153 (1989);
36. (d) I.H. Um, H.J. Kwon, D.S. Kwon, and J.Y. Park. J. Chem. Res. Miniprint, 1801 (1995); J. Chem. Res. Synop. 301 (1995).
37. (d) I.H. Um, H.J. Kwon, D.S. Kwon, and J.Y. Park. J. Chem. Res. Miniprint, 1801 (1995); J. Chem. Res. Synop. 301 (1995).
38. H.C. Brown and Y. Okamoto. J. Am. Chem. Soc. 80, 4979 (1958).
39. I.H. Um, E.K. Chung, and D.S. Kwon. Tetrahedron Lett. 38, 4787 (1997).
40. E.A. Castro, M. Cubillos, J.G. Santos, and J. Tellez. J. Org. Chem. 62, 2512 (1997).
41. M.J. Gresser and W.P. Jencks. J. Am. Chem. Soc. 99, 6963 (1977); 99, 6970 (1977).
42. M.J. Gresser and W.P. Jencks. J. Am. Chem. Soc. 99, 6963 (1977); 99, 6970 (1977).
43. E.A. Castro, F. Ibanez, J.G. Santos, and C. Ureta. J. Org. Chem. 12, 93 (1991).
44. C.D. Hubbard and J.F. Kirsch. Biochemistry, 11, 2483 (1972).
45. E. Buncel, I.H. Um, and S. Hoz,. J. Am. Chem. Soc. 111, 971 (1989).
46. I.H. Um, E.S. Yeom, H.J. Kwon, and D.S. Kwon. Bull. Korean Chem. Soc. 18, 865 (1997).