Aminolysis of aryl N-ethyl thionocarbamates: Cooperative effects of atom pairs O and S on the reactivity and mechanism

Journal of Organic Chemistry

Volumn 70, Issue 14, 2005, Pages 5624-5629

  Oh, Hyuck Keun ^a   Oh, Ji Young ^a   Sung, Dae Dong ^b   Lee, Ikchoon ^b,c  

^a Chonbuk National University   (South Korea)

^b Dong A University   (South Korea)

^c Inha University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ATOMS; ISOTOPES; ORGANIC COMPOUNDS;

AMINOLYSIS REACTIONS; CROSS INTERACTION CONSTANT; DEUTERATED BENZLYAMINE; THIONOCARBAMATES;

AMINO ACIDS;

ACETONITRILE; BENZYLAMINE; CARBAMIC ACID DERIVATIVE; OXYGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFUR; THIOCARBAMIC ACID DERIVATIVE; THIONEINE;

AMINOLYSIS; ARTICLE; CHEMICAL PARAMETERS; CHEMICAL REACTION KINETICS; CONFORMATIONAL TRANSITION; CROSS INTERACTION CONSTANT; HYDROGEN BOND; KINETIC ISOTOPE EFFECT; REACTION ANALYSIS;

EID: 22144451481     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050606b     Document Type: Article

References (66)

1. (a) Satterthwait, C. A.; Jencks, W. P. J. Am. Chem. Soc. 1974, 96, 7018.
2. (b) Castro, E. A.; Ibanez, F.; Santos, J. G.; Ureta, C. J. Org. Chem. 1993, 58, 4908.
3. (c) Castro, E. A.; Ureta, C. J. Chem. Soc., Perkin Trans. 2 1991, 63.
4. (d) Castro, E. A.; Ureta, C. J. Org. Chem. 1990, 55, 1676.
5. (e) Oh, H. K.; Shin, C. H.; Lee, I. Bull. Korean Chem. Soc. 1995, 16, 657.
6. (f) Oh, H. K.; Woo, S. Y.; Shin, C. H.; Park, Y. S.; Lee, I. J. Org. Chem. 1997, 62, 5780.
7. (g) Um, I.-H.; Kwon, D.-S.; Park, Y.-J. J. Chem. Res., Synop. 1995, 301.
8. (h) Um, I.-H.; Choi, K.-E.; Kwon, D.-S. Bull. Korean Chem. Soc. 1990, 11, 362.
9. (a) Gresser, M. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 6963.
10. (b) Castro, E. A.; Gil, F. J. J. Am. Chem. Soc. 1977, 99, 7611.
11. (c) Castro, E. A.; Aliga, M.; Campodonico, P. J.; Santos, J. G. J. Org. Chem. 2002, 67, 8911.
12. (d) Castro, E. A.; Araneda, C. A.; Santos, J. G. J. Org. Chem. 1997, 62, 126.
13. (e) Castro, E. A.; Andajar, M.; Taro, A.; Santos, J. G. J. Org. Chem. 2003, 68, 3608.
14. (f) Castro, E. A.; Munoz, P.; Santos, J. G. J. Org. Chem. 1999, 64, 8298.
15. (g) Oh, H. K.; Lee, Y. J.; Lee, I. Int. J. Chem. Kinet. 2000, 32, 132.
16. (h) Song, H. B.; Choi, M. H.; Koo, I. S.; Oh, H. K.; Lee, I. Bull. Korean Chem. Soc. 2003, 24, 91.
17. (i) Castro, E. A.; Pizarro, M. I.; Santos, J. G. J. Org. Chem. 1996, 61, 5982.
18. (a) Menger, F. M.; Glass, L. E. J. Org. Chem. 1974, 39, 2469.
19. (b) Shwali, A. S.; Harbash, A.; Sidky, M. M.; Hassaneen, H. M.; Elkaabi, S. S. J. Org. Chem. 1986, 51, 3498.
20. (c) Koh, H. J.; Kim, O. S.; Lee, H. W.; Lee, I. J. Phys. Org. Chem. 1997, 10, 725.
21. (d) Oh, H. K.; Park, J. E.; Sung, D. D.; Lee, I. J. Org. Chem. 2004, 69, 3150.
22. (e) Oh, H. K.; Oh, J. Y.; Sung, D. D.; Lee, I. Collect. Czech. Chem. Commun. 2004, 69, 2174.
23. (f) Oh, H. K.; Jin, Y. C.; Sung, D. D.; Lee, I. Org. Biomol. Chem. 2005, 3, 1240.
24. (a) Lee, I. Chem. Soc. Rev. 1990, 19, 317.
25. (b) Lee, I. Adv. Phys. Org. Chem. 1992, 27, 57.
26. Lee, I.; Sung, D. D. Curr. Org. Chem. 2004, 7, 557.
27. (a) Ritchie, C. D. In Solute-Solvent Interactions; Coetzee, J. F., Ritchie, C. D., Eds.; Marcel Dekker: New York, 1969; Chapter 4.
28. (b) Coetzee, J. F. Prog. Phys. Org. Chem. 1967, 4, 54.
29. (c) Spillane, W. J.; Hogan, G.; McGrath, P.; King, J.; Brack, C. J. Chem. Soc. Perkin Trans. 2 1996, 2099.
30. (d) Lee, I.; Kim, C. K.; Han, I. S.; Lee, H. W.; Kim, W. K.; Kim, Y. B. J. Phys. Chem. B 1999, 103, 7302.
31. Oh, H. K.; Ku, M. H.; Lee, H. W.; Lee, I. J. Org. Chem. 2002, 67, 3874.
32. Oh, H. K.; Park, J. E.; Sung, D. D.; Lee, I. J. Org. Chem. 2004, 69, 9285.
33. McWeeny, R. Coulson's Valence; Oxford University Press: Oxford, 1979; p 163.
34. (a) McKinnon, D. M.; Queen, A. Can. J. Chem. 1972, 50, 1401.
35. (b) Ruff, F.; Csizmadia, I. G. Organic Reactions. Equilibria, Kinetics, and Mechanism; Elsevier: Amsterdam, 1994; p 330.
36. (a) Castro, E. A.; Ruiz, M. G.; Salinas, S.; Santos, J. G. J. Org. Chem. 1999, 64, 4817.
37. (b) Castro, E. A.; Cubillos, M.; Santos, J. G. J. Org. Chem. 1997, 62, 4395.
38. (c) Castro, E. A.; Ruiz, M. G.; Santos, J. G. Int. J. Chem. Kinet. 2001, 33, 281.
39. (a) Yew, K. H.; Koh, H. J.; Lee, H. W.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1995, 2263.
40. (b) Oh, H. K.; Ha, J. S.; Sung, D. D.; Lee, I. J. Org. Chem. 2004, 69, 8219.
41. Epiotis, N. D.; Cherry, W. R.; Shaik, S.; Yates, R. L.; Bernardi, F. Structural Theory of Organic Chemistry; Springer-Verlag: Berlin, 1977; p 18.
42. (a) Castro, E. A.; Cubillos, M.; Santos, J. G.; Tellez, J. J. Org. Chem. 1997, 62, 2512.
43. (b) Castro, E. A.; Ibanez, F.; Santos, J. G.; Ureta, C. J. Chem. Soc. Perkin Trans. 2 1996, 1919.
44. (c) Lee, I.; Kim, C. K.; Li, H. G.; Sohn, C. K.; Kim, C.K.; Lee, H. W.; Lee, B.-S. J. Am. Chem. Soc. 2000, 122, 11162.
45. Reference 13, p 19.
46. Oh, H. K.; Lee, J. Y.; Lee, I. Bull. Korean Chem Soc. 1998, 19, 1198.
47. Koh, H. J.; Lee, J.-W.; Lee, H. W.; Lee, I. New J. Chem. 1997, 21, 447.
48. (a) Oh, H. K.; Lee, J. Y.; Lee, H. W.; Lee, I. New J. Chem. 2002, 26, 473.
49. (b) Koh, H. J.; Shin, C. H.; Lee, H. W.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1998, 1329.
50. (a) Pross, A. Adv. Phys. Org. Chem. 1997, 14, 69.
51. (b) Buncel, E.; Wilson, H. J. Chem. Educ. 1987, 64, 475.
52. (a) Castro, E. A.; Pavez, P.; Santos, J. G. J. Org. Chem. 2001, 66, 3129.
53. (b) Stefanidis, D.; Cho, S.; Dhe-Paganon, S.; Jencks, W. P. J. Am. Chem. Soc. 1993, 115, 1659.
54. (a) Castro, E. A.; Ibanez, F.; Santos, J. G. J. Org. Chem. 1991, 56, 4819.
55. (b) Castro, E. A.; Leandro, L.; Millan, R.; Santos, J. G. J. Org. Chem. 1999, 64, 1953.
56. (a) Skoog, M. T.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 7597.
57. (b) Bourne, N.; Williams, A. J. Am. Chem. Soc. 1984, 106, 7591.
58. (a) Ba-Saif, S.; Luthra, A. K.; Williams, A. J. Am. Chem. Soc. 1989, 111, 2647.
59. (b) Colthurst, M. J.; Nanni, M.; Williams, A. J. Chem. Soc., Perkin Trans. 2 1996, 2285.
60. (a) Maude, A. B.; Williams, A. J. Chem. Soc., Perkin Trans. 2 1997, 179.
61. (b) Castro, E. A.; Cubillos, M.; Santos, J. G. J. Org. Chem. 1998, 63, 6820.
62. Castro, E. A.; Cubillos, M.; Munoz, G.; Santos, J. G. Int. J. Chem. Kinet. 1994, 26, 571.
63. Lee, I. Chem. Soc. Rev. 1995, 24, 571.
64. Lee, I.; Shim, C. S.; Chung, S. Y.; Kim, H. Y.; Lee, H. W. J. Chem. Soc., Perkin Trans. 2 1988, 1919.
65. (a) Guggenheim, E. A. Philos. Mag. 1926, 2, 538.
66. (b) Moor, J. W.; Pearson, R. G. Kinetics and Mechanism, 3rd ed.; Wiley: New York, 1981; p 71.