Kinetics and mechanism of the aminolysis of S-aryl O-ethyl dithiocarbonates in acetonitrile

Collection of Czechoslovak Chemical Communications

Volumn 69, Issue 12, 2004, Pages 2174-2182

  Oh, Hyuk 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

Aminolysis; Concerted mechanism; Cross interaction constants; Kinetic isotope effects; Reaction mechanisms; S Aryl O ethyl dithiocarbonates

Indexed keywords

ACETONITRILE; AMPHOLYTE; BENZYLAMINE; CARBONIC ACID DERIVATIVE; THIOL DERIVATIVE;

AMINOLYSIS; ARTICLE; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; HYDROGEN BOND; MOLECULAR MECHANICS; PHASE TRANSITION;

EID: 14844283831     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20042174     Document Type: Article

References (39)

1. a) Jencks W. P.: Chem. Rev. 1985, 85, 511;
2. b) Gresser M., Jencks W. P.: J. Am. Chem. Soc. 1977, 99, 6963;
3. c) Gresser M., Jencks W. P.: J. Am. Chem. Soc. 1977, 99, 6970;
4. d) Castro E. A., Ureta C.: J. Org. Chem. 1989, 54, 2153;
5. e) Castro E. A., Ureta C.: J. Org. Chem. 1990, 55, 1676;
6. f) Koh H. J., Han K. L., Lee I.: J. Org. Chem. 1999, 64, 4783;
7. g) Oh H. K., Ku M. H., Lee H. W., Lee I.: J. Org. Chem. 2002, 67, 3874.
8. Castro E. A., Munoz P., Santos J. G.: J. Org. Chem. 1999, 64, 8298.
9. a) Castro E. A., Ibanez F., Salas M., Santos J. G.: J. Org. Chem. 1991, 56, 4819;
10. b) Castro E. A., Salas M., Santos J. G.: J. Org. Chem. 1994, 59, 30.
11. a) Lee I.: Adv. Phys. Org. Chem. 1992, 27, 57;
12. b) Lee I.: Chem. Soc. Rev. 1990, 19, 317;
13. c) Lee I., Lee H. W.: Collect. Czech. Chem. Commun. 1999, 64, 1529.
14. Koh H. J., Lee J.-W., Lee H. W., Lee I.: Can. J. Chem. 1998, 76, 710.
15. a) Oh H. K., Lee Y. H., Lee I.: Int. J. Chem. Kinet. 2000, 32, 131;
16. b) Oh H. K., Lee J.-Y., Park Y. S., Lee I.: Int. J. Chem. Kinet. 1998, 30, 419.
17. a) Coetzee J. F.: Prog. Phys. Org. Chem. 1965, 4, 45;
18. b) Spillane W. J., Hogan G., McGrath P., King J., Brack C.: J. Chem. Soc., Perkin Trans. 2 1996, 2099;
19. c) Lee I., Kim C. K., Han I. S., Lee H. W., Kim W. K., Kim Y. B.: J. Phys. Chem. B 1999, 103, 7302.
20. 1e and Oh H. J., Park J. E., Sung D. D., Lee I.: J. Org. Chem. 2004, 69, 3150.
21. Oh H. K., Woo S. Y., Shin C. H., Park Y. S., Lee I.: J. Org. Chem. 1997, 62, 5780.
22. Oh H. K., Shin C. H., Lee I.: Bull. Korean Chem. Soc. 1995, 16, 657.
23. 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.
24. a) Reed A. E., Curtiss L. A., Weinhold F.: Chem. Rev. 1998, 88, 899;
25. b) Epiotis N. D., Cherry W. R., Shaik S., Yates R., Bernardi F.: Structural Theory of Organic Chemistry, Part I. Springer-Verlag, Berlin 1977;
26. c) Lee I.: Int. Rev. Phys. Chem. 2003, 22, 263.
27. a) Skoog M. T., Jencks W. P.: J. Am. Chem. Soc. 1984, 106, 7597;
28. b) Bourne N., Williams A.: J. Am. Chem. Soc. 1984, 106, 7591.
29. Ba-Saif S., Luthra A. K., Williams A.: J. Am. Chem. Soc. 1989, 111, 2647.
30. This work.
31. Castro E. A., Ibanez F., Salas M., Santos J. G., Sepulveda P.: J. Org. Chem. 1993, 58, 459.
32. Castro E. A., Pizarro M. I., Santos J. G.: J. Org. Chem. 1996, 61, 5982.
33. Castro E. A., Araneda C. A., Santos J. G.: J. Org. Chem. 1997, 62, 126.
34. Castro E. A., Leandro L., Millan P., Santos J. G.: J. Org. Chem. 1999, 64, 1953.
35. a) Lee I., Sung D. D.: Curr. Org. Chem. 2004, 8, 557;
36. b) Oh H. K., Kim I. K., Sung D. D., Lee I.: Org. Biomol. Chem. 2004, 2, 1213.
37. Lee I.: Chem. Soc. Rev. 1995, 24, 223.
38. Isaacs N. S.: Physical Organic Chemistry, 2nd ed., Chap. 10. Longman, Harlow 1995.
39. Castro E. A., Cubillos M., Ibanez F., Moraga I., Santos J. G.: J. Org. Chem. 1993, 58, 5400.