Correlation of the rates of solvolysis of 4-morpholinecarbonyl chloride using the extended Grunwald-Winstein equation

Bulletin of the Korean Chemical Society

Volumn 31, Issue 7, 2010, Pages 1963-1967

  Kim, Ran ^a   Ali, Dildar ^a,b   Lee, Jong Pal ^a,c   Yang, Kiyull ^a   Koo, In Sun ^a  

^a Gyeongsang National University   (South Korea)

^b UNIVERSITY OF BALOCHISTAN   (Pakistan)

^c Dong A University   (South Korea)

Author keywords

4 morpholinecarbonyl chloride (MPC); Addition elimination (A E); Grunwald Winstein equation; Ionization (I); Ksie

Indexed keywords

ADDITION-ELIMINATION; ADDITION-ELIMINATION (A-E); DEUTERIUM ISOTOPE EFFECT; GRUNWALD-WINSTEIN EQUATION; IONIZATION MECHANISMS; IONIZING POWER; METHANOLYSIS; NEGATIVE ENTROPIES; NUCLEOPHILICITIES; TRIFLUOROETHANOL;

ACETONE; BINARY MIXTURES; CHLORINE COMPOUNDS; DEUTERIUM; DISSOCIATION; ETHANOL; METHANOL; MODEL PREDICTIVE CONTROL; PARTICLE DETECTORS; SOLVENTS;

IONIZATION OF LIQUIDS;

EID: 77954948092     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.7.1963     Document Type: Article

References (67)

1. Grunwald, E.; Winstein, S. J. Am. Chem. Soc. 1948, 70, 846.
2. Winstein, S.; Grunwald, E.; Jones, H. W. J. Am. Chem. Soc. 1951, 73, 2700.
3. Bentley, T. W.; Llewellyn, G. Prog. Phys. Org. Chem. 1990, 17, 121.
4. Kevill, D. N.; D'Souza, M. J. J. Chem. Res. Synop. 1993, 174.
5. Lomas, J. S.; D'Souza, M. J.; Kevill, D. N. J. Am. Chem. Soc. 1995, 117, 5891.
6. Bentley, T. W.; Carter, G. E.; Harris, H. C. J. Chem. Soc., Chem. Commun. 1984, 388.
7. Bentley, T. W.; Carter, G. E.; Harris, H. C. J. Chem. Soc., Perkin Trans. 2 1985, 983.
8. Bentley, T. W.; Harris, H. C. J. Chem. Soc., Perkin Trans. 2 1986, 619.
9. Bentley, T. W.; Harris, H. C.; Koo, I. S. J. Chem. Soc., Perkin Trans. 2 1988, 783.
10. Swain, C. G.; Mosely, R. B.; Bown, D. E. J. Am. Chem. Soc. 1955, 77, 3731.
11. Koo, I. S.; Bentley, T. W.; Kang, D. H.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1991, 173.
12. Koo, I. S.; Bentley, T. W.; Llewellyn, G.; Yang, K. J. Chem. Soc., Perkin Trans. 2 1991, 1175.
13. Koo, I. S.; Kwon, E.; Choi, H.; Yang, K.; Park, J. K.; Lee, J. P.; Lee, I.; Bentley, T. W. Bull. Korean Chem. Soc. 2007, 28, 2377.
14. Winstein, S.; Fainberg, A. H.; Grunwald, E. J. Am. Chem. Soc. 1957, 79, 4146.
15. Fainberg, A. H.; Winstein, S. J. Am. Chem. Soc. 1957, 79, 1957.
16. Koo, I. S.; Yang, K.; Kang, K.; Lee, I. Bull. Korean Chem. Soc. 1998, 19, 968.
17. Koo, I. S.; Lee, J. S.; Yang, K.; Kang, K.; Lee, I. Bull. Korean Chem. Soc. 1999, 20, 573.
18. Kevill, D. N.; Ismail, NHJ.; D'Souza, M. J. J. Org. Chem. Soc. 1994, 59, 6303.
19. Kevill, D. N.; D'Souza, M. J. J. Chem. Soc., Perkin Trans. 2 1995, 973.
20. Kevill, D. N.; D'Souza, M. J. J. Chem. Soc., Perkin Trans. 2 1997, 257.
21. Kevill, D. N.; Bond, M. W.; D'Souza, M. J. J. Org. Chem. 1997, 62, 7869.
22. Kevill, D. N. Development and Uses of Scales of Solvent Nucleophilicity. In Advances in Quantitative Structure-Property Relationships; Charton, M., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 1, 81-115.
23. Kevill, D. N.; Anderson, S. W. J. Org. Chem. 1991, 56, 1845.
24. Kevill, D. N.; D'Souza, M. J. J. Chem. Soc., Perkin Trans. 2 2002, 240.
25. Kyong, J. B.; Rhu, C. J.; Kim, Y. G.; Kevill, D. N. J. Phys. Org. Chem. 2007, 20, 525.
26. Kevill, D. N.; D'Souza, M. J. J. Phys. Org. Chem. 2002, 15, 881.
27. Lee, I.; Koo, I. S.; Sohn, S. C.; Lee, H. H. Bull. Korean Chem. Soc. 1982, 3, 92.
28. Lee, I.; Sung, D. D.; Uhm, T. S.; Ryu, Z. H. J. Chem. Soc., Perkin Trans. 2 1989, 1697.
29. Bentley, T. W.; Harris, H. C.; Koo, I. S. J. Chem. Soc., Perkin Trans. 2 1988, 783.
30. Bentley, T. W.; Harris, H. C. J. Org. Chem. 1988, 53, 724.
31. Bentley, T. W.; Koo, I. S. J. Chem. Soc., Perkin Trans. 2 1989, 1385.
32. Bentley, T. W.; Koo, I. S.; Norman, S. J. J. Org. Chem. 1991, 56, 1604.
33. Koo, I. S.; Lee, J. S.; Yang, K.; Kang, K.; Lee, I. Bull. Korean Chem. Soc. 1999, 20, 573.
34. Koo, I. S.; Yang, K.; Koo, J. C.; Park, J. K.; Lee, I. Bull. Korean Chem. Soc. 1997, 18, 1017.
35. Koo, I. S.; Yang, K.; Kang, K.; Lee, I. Bull. Korean Chem. Soc. 1998, 19, 968.
36. Kevill, D. N.; Kim, J. C.; Kyong, J. B. J. Chem. Research 1999, 150.
37. An, S. K.; Yang, T. S.; Cho, J. M.; Yang, K.; Lee, J. P.; Bentley, T. W.; Lee, I.; Koo, I. S. Bull. Korean Chem. Soc. 2002, 23, 1445.
38. Kevill, D. N.; D'Souza, M. J. J. Org. Chem. 1998, 63, 2120.
39. Koo, I. S.; Bentley, T. W.; Lee, I. J. Korean Chem. Soc. 1990, 34, 304.
40. Oh, J.; Yang, K.; Koo, I. S.; Lee, I. J. Chem. Res. 1993, 310.
41. Bentley, T. W.; Llewellyn, G.; Ryu, Z. H. J. Org. Chem. 1998, 63, 4654.
42. N2.
43. McLennan, D. J.; Martin, P. L. J. Chem. Soc., Perkin Trans. 2 1982, 1099.
44. Liu, K.-T.; Duann, Y. F.; Hou, S. H. J. Chem. Soc., Perkin Trans. 2 1998, 2181.
45. Liu, K.-T.; Chen, H.-I. J. Chem. Soc., Perkin Trans. 2 2000, 893.
46. Ryu, Z. H.; Shin, S. H.; Lim, G. T.; Lee, J. P. Bull. Korean Chem. Soc. 2004, 25, 307.
47. Koo, I. S.; An, S. K.; Yang, K.; Koh, H. J.; Choi, M. H.; Lee, I. Bull. Korean Chem. Soc. 2001, 22, 842.
48. Ryu, Z. H.; Bentley, T. W. Bull. Korean Chem. Soc. 2008, 29, 2145.
49. Kevill, D. N.; Ryu, Z. H.; Niedermeyer, M. A.; Koyoshi, F.; D'Souza, M. J. J. Phys. Org. Chem. 2007, 20, 431.
50. Ryu, Z. H.; Lee, S. W.; D'Souza, M. J.; Yaakoubd, L.; Feld, S. E.; Kevill, D. N. Int. J. Mol. Sci. 2008, 9, 2639.
51. Kyong, J. B.; Yoo, J. S.; Kevill, D. N. J. Org. Chem. 2003, 68, 3425.
52. Kevill, D. N.; D'Souza, M. J. J. Chem. Soc., Perkin Trans. 2 1997, 1721.
53. Kyong, J. B.; Won, H.; Kevill, D. N. Int. J. Mol. Sci. 2005, 6, 87.
54. Kyong, J. B.; Kim, Y. G.; Kim, D. K.; Kevill, D. N. Bull. Korean Chem. Soc. 2000, 21, 662.
55. Kyong, J. B.; Park, B. C.; Kim, C. B.; Kevill, D. N. J. Org. Chem. 2000, 65, 8051.
56. Johnson, S. Adv. Phys. Org. Chem. 1967, 5, 237.
57. Bacaloglu, R.; Daescu, C.; Ostrogovich, G. J. Chem. Soc., Perkin Trans. 2 1972, 1011.
58. D'Souza, M. J.; Kevill, D. N.; Bentley, T. W.; Devaney, A. C. J. Org. Chem. 1995, 60, 1632.
59. Kevill, D. N.; Bond, M. W.; D'Souza, M. J. J. Phys. Org. Chem. 1998, 11, 273.
60. Kevill, D. N.; Rudolph, T. M.; D'Souza, M. J. J. Phys. Org. Chem. 2000, 13, 192.
61. Kosower, E. M. J. Am. Chem. Soc. 1958, 80, 3253.
62. Kosower, E. M. J. Am. Chem. Soc. 1958, 80, 3267.
63. Frost, A.; Pearson, R. G. Kinetic and Mechanism, 2nd ed.; Wiley: New York, 1961; Chap 7.
64. Queen, A. Can. J. Chem. 1967, 45, 1619.
65. Yew, K. H.; Koh, H. J.; Lee, H. W. J. Chem. Soc., Perkin Trans. 2 1995, 2263.
66. Koo, I. S.; Yang, K.; Kang, K.; Oh, H. J.; Lee, I. Bull. Korean Chem. Soc. 1996, 17, 520.
67. Kevill, D. N.; D'Souza, M. J. J. Org. Chem. 1998, 63, 2120.