Kinetics and mechanism of the pyridinolysis of aryl phenyl chlorothiophosphates in acetonitrile

Bulletin of the Korean Chemical Society

Volumn 32, Issue 4, 2011, Pages 1138-1142

  Ul Hoque, Md Ehtesham ^a   Dey, Shuchismita ^a   Kim, Chan Kyung ^a   Lee, Hai Whang ^a  

^a Inha University   (South Korea)

Author keywords

Biphasic concave upward downward free energy correlation; Phosphoryl transfer reaction; Pyridinolysis; Y aryl phenyl chlorothiophosphates

Indexed keywords

BIPHASIC; BOND FORMATION; BOND-BREAKING; BREAK-POINTS; CROSS-INTERACTION CONSTANTS; ELECTROPHILES; ENERGY CORRELATION; HAMMETT PLOTS; KINETIC STUDY; KINETICS AND MECHANISM; NON-LINEAR FREE ENERGY; PHOSPHORYL TRANSFER; PYRIDINOLYSIS; RATE-LIMITING STEPS; Y-ARYL PHENYL CHLOROTHIOPHOSPHATES;

ACETONITRILE; FREE ENERGY; NUCLEOPHILES; PYRIDINE;

REACTION KINETICS;

EID: 79954593799     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2011.32.4.1138     Document Type: Article

References (56)

1. (a)Guha, A. K.; Lee, H. W.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1999, 765.
2. (b) Lee, H. W.; Guha, A. K.; Lee, I. Int. J. Chem. Kinet. 2002, 34, 632.
3. (c) Hoque, M. E. U.; Dey, S.; Guha, A. K.; Kim, C. K.; Lee, B. S.; Lee, H. W. J. Org. Chem. 2007, 72, 5493.
4. (d)Hoque, M. E. U.; Lee, H. W. Bull. Korean Chem. Soc. 2007, 28, 936.
5. (e) Dey, N. K.; Han, I. S.; Lee, H. W. Bull. Korean Chem. Soc. 2007, 28, 2003.
6. (f) Hoque, M. E. U.; Dey, N. K.; Kim, C. K.; Lee, B. S.; Lee, H. W. Org. Biomol. Chem. 2007, 5, 3944.
7. (g) Dey, N. K.; Hoque, M. E. U.; Kim, C. K.; Lee, B. S.; Lee, H. W. J. Phys. Org. Chem. 2008, 21, 544.
8. (h) Lumbiny, B. J.; Lee, H. W. Bull. Korean Chem. Soc. 2008, 29, 2065.
9. (i) Dey, N. K.; Hoque, M. E. U.; Kim, C. K.; Lee, B. S.; Lee, H. W. J. Phys. Org. Chem. 2009, 22, 425.
10. (j) Dey, N. K.; Kim, C. K.; Lee, H. W. Bull. Korean Chem. Soc. 2009, 30, 975.
11. (k) Hoque, M. E. U.; Guha, A. K.; Kim, C. K.; Lee, B. S.; Lee, H. W. Org. Biomol. Chem. 2009, 7, 2919.
12. (l) Dey, N. K.; Lee, H. W. Bull. Korean Chem. Soc. 2010, 31, 1403.
13. (m) Dey, N. K.; Kim, C. K.; Lee, H. W. Org. Biomol. Chem. 2011, 9, 717.
14. (a) Guha, A. K.; Lee, H. W.; Lee, I. J. Org. Chem. 2000, 65, 12.
15. (b) Lee, H. W.; Guha, A. K.; Kim, C. K.; Lee, I. J. Org. Chem. 2002, 67, 2215.
16. (c) Adhikary, K. K.; Lee, H. W.; Lee, I. Bull. Korean Chem. Soc. 2003, 24, 1135.
17. (d)Hoque, M. E. U.; Dey, N. K.; Guha, A. K.; Kim, C. K.; Lee, B. S.; Lee, H. W. Bull. Korean Chem. Soc. 2007, 28, 1797.
18. Adhikary, K. K.; Lumbiny, B. J.; Kim, C. K.; Lee, H. W. Bull. Korean Chem. Soc. 2008, 29, 851.
19. (f) Lumbiny, B. J.; Adhikary, K. K.; Lee, B. S.; Lee, H. W. Bull. Korean Chem. Soc. 2008, 29, 1769.
20. (g) Dey, N. K.; Hoque, M. E. U.; Kim, C. K.; Lee, H. W. J. Phys. Org. Chem. 2010, 23, 1022.
21. (h) Dey, N. K.; Adhikary, K. K.; Kim, C. K.; Lee, H. W. Bull. Korean Chem. Soc. 2010, 31, 3856.
22. (i) Guha, A. K.; Kim, C. K.; Lee, H. W. J. Phys. Org. Chem. DOI.10.1002/poc.1788.
23. (j) Dey, N. K.; Kim, C. K.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 709.
24. (a) 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.
25. (b) Han, I. S.; Kim, C. K.; Lee, H. W. Bull. Korean Chem. Soc. 2011, 32, 889.
26. (a) Lee, I.; Kim, C. K.; Han, I. S.; Lee, H. W.; Kim, W. K.; Kim, Y. B. J. Phys. Chem. B 1999, 103, 7302.
27. (b) Coetzee, J. F. Prog. Phys. Org. Chem. 1967, 4, 45.
28. (a) Lee, I. Chem. Soc. Rev. 1990, 19, 317.
29. (b) Lee, I. Adv. Phys. Org. Chem. 1992, 27, 57.
30. (c) Lee, I.; Lee, H. W. Collect. Czech. Chem. Commun. 1999, 64, 1529.
31. The obtained values of pXY are all calculated with twelve rate constants. In general, more than twenty rate constants are employed to minimize the error.
32. The TSf would be significantly distorted TBP-5C; even hard to call TBP-5C and rather similar to cis-basal; Thatcher, G. R. J.; Kluger, R. Adv. Phys. Org. Chem. 1989, 25, 99.
33. Hall, C. R.; Inch, T. D. Tetrahedron 1980, 36, 2059.
34. (b)Ref. 3b.
35. (a) Williams, A. Free Energy Relationships in Organic and Bioorganic Chemistry; RSC: Cambridge, UK, 2003; Chapter 7.
36. (b) Ruff, A.; Csizmadia, I. G. Organic Reactions Equilibria, Kinetics and Mechanism; Elsevier: Amsterdam, Netherlands, 1994; Chapter 7.
37. (c) Oh, H. K.; Lee, J. M.; Lee H. W.; Lee, I. Int. J. Chem. Kinet. 2004, 36, 434.
38. (d) Oh, H. K.; Park, J. E.; Lee, H. W. Bull. Korean Chem. Soc. 2004, 25, 1041.
39. (e) Oh, H. K.; Ku, M. H.; Lee, H. W.; Lee, I. J. Org. Chem. 2002, 67, 8995.
40. (f) Castro, E. A.; Angel, M.; Campodonico, P.; Santos, J. G. J. Org. Chem. 2002, 67, 8911.
41. (g) Castro, E. A.; Pavez, P.; Santos, J. G. J. Org. Chem. 2002, 67, 4494.
42. (h) Oh, H. K.; Ku, M. H.; Lee, H. W.; Lee, I. J. Org. Chem. 2002, 67, 3874.
43. (i) Castro, E. A.; Pavez, P.; Santos, J. G. J. Org. Chem. 2002, 67, 3129.
44. (j) Castro, E. A.; Pavez, P.; Arellano, D.; Santos, J. G. J. Org. Chem. 2001, 66, 6571.
45. (k) Spillane, W. J.; McGrath, P.; Brack, C.; O'Byrne, A. B. J. Org. Chem. 2001, 66, 6313.
46. (l) Koh, H. J.; Han, K. L.; Lee, H. W.; Lee, I. J. Org. Chem. 2000, 65, 4706.
47. (m) Humeres, E.; Debacher, N. A.; Sierra, M. M. D.; Franco J. D.; Shutz, A. J. Org. Chem. 1998, 63, 1598.
48. (n) Baynham, A. S.; Hibbert, F.; Malana, M. A. J. Chem. Soc., Perkin Trans 2 1993, 1711.
49. Charton, M. Prog. Phys. Org. Chem. 1987, 16, 287.
50. Hehre, W. J.; Random, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; Chapter 4.
51. (a) Hondal, R. J.; Bruzik, K. S.; Zhao, Z.; Tsai, M. D. J. Am. Chem. Soc. 1997, 119, 5477.
52. (b) Holtz, K. M.; Catrina, I. E.; Hengge, A. C.; Kantrowitz, E. R. Biochemistry 2000, 39, 9451.
53. (c) Omakor, J. E.; Onyido, I.; vanLoon, G. W.; Buncel, E. J. Chem. Soc., Perkin Trans. 2 2001, 324.
54. (d) Gregersen, B. A.; Lopez, X.; York, D. M. J. Am. Chem. Soc. 2003, 125, 7178.
55. (e) Onyido, I.; Swierczek, K.; Purcell, J.; Hengge, A. C. J. Am. Chem. Soc. 2005, 127, 7703. 324.
56. Liu, Y.; Gregersen, B. A.; Hengge, A. C.; York, D. M. Biochemistry 2006, 45, 10043.