The effect of medium on rate and mechanism: Aminolysis of O-4-nitrophenyl thionobenzoate in MeCN and H2O

Journal of Organic Chemistry

Volumn 68, Issue 20, 2003, Pages 7742-7746

  Um, Ik Hwan ^a   Seok, Jin A ^a   Kim, Han Tae ^b   Bae, Sun Kun ^b  

^a Ewha Womans University   (South Korea)

^b Kunsan National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; RATE CONSTANTS; SPECTROPHOTOMETRY;

AMINOLYSIS;

ORGANOMETALLICS;

ACETONITRILE; AMINE; AMPHOLYTE; BENZOIC ACID DERIVATIVE; O 4 NITROPHENYL THIONOBENZOATE; UNCLASSIFIED DRUG; WATER;

ALKALINITY; ARTICLE; CHEMICAL REACTION; PROTON TRANSPORT; REACTION ANALYSIS; SPECTROPHOTOMETRY;

EID: 0141543645     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034637n     Document Type: Article

References (38)

1. Campbell, P.; Lapinskas, B. A. J. Am. Chem. Soc. 1977, 99, 5378-5382.
2. (a) Um, I. H.; Lee, S. E.; Kwon, H. J. J. Org. Chem. 2002, 67, 8999-9005.
3. (b) Um, I. H.; Kwon, H. J.; Kwon, D. S.; Park, J. Y. J. Chem. Res., Synop. 1995, 301;
4. J. Chem. Res., Miniprint 1995, 1801-1817.
5. (a) Castro, E. A. Chem. Rev. 1999, 99, 3505-3524.
6. (b) Castro, E. A.; Galvez, A.; Leandro, L.; Santos, J. G. J. Org. Chem. 2002, 67, 4309-4315.
7. (c) Castro, E. A.; Leandro, L.; Quesieh, N.; Santos, J. G. J. Org. Chem. 2001, 66, 6130-6135.
8. (d) Castro, E. A.; Garcia, P.; Leandro, L.; Quesieh, N.; Rebolledo, A.; Santos, J. G. J. Org. Chem. 2000, 65, 9047-9053.
9. (e) Castro, E. A.; Saavedra, C.; Santos, J. G.; Umana, M. I. J. Org. Chem. 1999, 64, 5401-5407.
10. (a) Oh, H. K.; Woo, S. Y.; Shin, C. H.; Park, Y. S.; Lee, I. J. Org. Chem. 1997, 62, 5780-5784.
11. (b) Oh, H. K.; Ku, M. H.; Lee, H. W.; Lee, I. J. Org. Chem. 2002, 67, 8995-8998.
12. (c) Lee, I.; Lee, H. W.; Lee, B. C.; Choi, J. H. Bull. Korean Chem. Soc. 2002, 23, 201-205.
13. (d) Oh, H. K.; Kim, K. S.; Lee, H. W.; Lee, I. New J. Chem. 2001, 25, 313-317.
14. Pfeiffer, M. J.; Hanna, S. B. J. Org. Chem. 1993, 58, 735-740.
15. Kwon, D. S.; Park, H. S.; Um, I. H. Bull. Korean Chem. Soc. 1991, 12, 93-97.
16. (a) Satterthwait, A. C.; Jencks, W. P. J. Am. Chem. Soc. 1974, 96, 7018-7031.
17. (b) Gresser, M. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 6963-6970.
18. (c) Jencks, W. P.; Brant, S. R.; Gandler, J. R.; Fendrich, G.; Nakamura, C. J. Am. Chem. Soc. 1982, 104, 7045-7051.
19. (d) Stefanidis, D.; Cho, S.; Dhe-Paganon, S.; Jencks, W. P. J. Am. Chem. Soc. 1993, 115, 1650-1656.
20. Oh, H. K.; Kim, K. S.; Lee, H. W.; Lee, I. J. Chem. Soc., Perkin Trans. 2 2000, 2306-2310.
21. (a) Castro, E. A.; Ibanez, F.; Santos, J. G.; Ureta, C. J. Org. Chem. 1993, 58, 4908-4912.
22. (b) Castro, E. A.; Ibanez, F.; Santos, J. G.; Ureta, C. J. Chem. Soc., Perkin Trans. 2 1991, 1919-1924.
23. (a) Maude, A. B.; Williams, A. J. Chem. Soc., Perkin Trans. 2 1997, 179-183.
24. (b) Maude, A. B.; Williams, A. J. Chem. Soc., Perkin Trans. 2 1995, 691-696.
25. (c) Talvik, A. T.; Tuulmets, A.; Vanino, E. J. Phys. Org. Chem. 1999, 12, 747-750.
26. (d) Jedrzejczak, M.; Motie, R. E.; Satchell, D. J. Chem. Soc., Perkin Trans. 2 1993, 599-600.
27. (a) Haberfield, P.; Cincotta, J. J. J. Org. Chem. 1990, 55, 1334-1338.
28. (b) Hogan, J. C.; Grandour, R. D. J. Org. Chem. 1991, 56, 2821-2826.
29. (c) Hogan, J. C.; Grandour, R. D. J. Org. Chem. 1992, 57, 55-61.
30. Menger, F. M.; Smith, J. H. J. Am. Chem. Soc. 1972, 94, 3824-3829.
31. Bell, R. P. The Proton in Chemistry; Methuen: London, UK, 1959; p159.
32. (a) Parker, A. J. Chem. Rev. 1969, 69, 1-32.
33. (b) Buncel, E.; Wilson, H. Adv. Phys. Org. Chem. 1977, 14, 133-202.
34. (c) Um, I. H.; Buncel, E. J. Org. Chem. 2000, 65, 577-582.
35. (d) Um, I. H.; Lee, E. J.; Buncel, E. J. Org. Chem. 2001, 66, 4859-4864.
36. (e) Um, I. H.; Buncel, E. J. Am. Chem. Soc. 2001, 123, 11111-11112.
37. Spillane, W. J.; McGrath, P.; Brack, C.; O'Byrne, A. B. J. Org. Chem. 2001, 66, 6313-6316.
38. Um, I. M.; Min, J. S.; Ahn J. A.; Hahn, H. J. J. Org. Chem. 2000, 65, 5659-5663.