Kinetics and mechanism of the aminolysis of aryl phenyl chlorothiophosphates with anilines

Journal of Organic Chemistry

Volumn 72, Issue 15, 2007, Pages 5493-5499

  Ul Hoque, Md Ehtesham ^a   Dey, Shuchismita ^a,b   Guha, Arun Kanti ^a,c   Chan, Kyung Kim ^a   Lee, Bon Su ^a   Hai, Whang Lee ^a  

^a Inha University   (South Korea)

^b SOUTHEAST UNIVERSITY   (Bangladesh)

^c City University   (Bangladesh)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; AMMONIA; ANILINE; ISOTOPES; NUCLEOPHILES; REACTION KINETICS;

AMINOLYSIS; ARYL PHENYL CHLOROTHIOPHOSPHATES (1); KINETIC ISOTOPE EFFECTS; SOLVATION EFFECT;

PHOSPHORUS COMPOUNDS;

ACETONITRILE; AMMONIA; ANILINE; PHOSPHOROTHIOIC ACID DERIVATIVE;

AMINOLYSIS; ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION KINETICS; ENERGY TRANSFER; HYDROGEN BOND; REACTION ANALYSIS; SOLVATION;

AMINES; ANILINE COMPOUNDS; KINETICS; MODELS, MOLECULAR; PHOSPHATES;

EID: 34547130551     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0700934     Document Type: Article

References (89)

1. (a) Nelson, R. C. J. - Assoc. Off. Anal. Chem. 1967, 50, 922.
2. (b) Stewart, J. P. Proc. Pap. Annu. Conf. Calif. Mosq. Control Assoc. 1975, 43, 37.
3. (c) Greenhalgh, R.; Dhawson, K. L.; Weinberg, P. J. Agric. Food Chem. 1980, 28, 102.
4. (d) Engel, R., Ed. Handbook of Organophosphorus Chemistry; Marcel Dekker: New York, 1992; p 465.
5. (e) Kamiya, M.; Nakamura, K.; Sasaki, C. Chemosphere 1995, 30, 653.
6. (f) Vale, J. A. Toxicol. Lett. 1998, 102-103, 649.
7. (g) Quin, L. D.; Quin, G. S. A Guide to Organophosphorus Chemistry; Wiley: New York, 2000; Chapter 11.
8. (h) Vayron, P.; Rebard, P.-Y.; Taran, F.; Créminon, C.; Frobert, Y.; Grassi, J.; Mioskowski, C. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 7058.
9. (i) Um, I. H.; Jeon, S. E.; Baek, M. H.; Park, H. R. Chem. Commun. 2003, 24, 3016.
10. (j) Lambert, W. E.; Lasarev, M.; Muniz, J.; Scherer, J.; Rothlein, J.; Santana, J.; McCauley, L. Environ. Health Perspect. 2005, 113, 504.
11. (k) Seger, M. R.; Maciel, G. E. Environ. Sci. Technol. 2006, 40, 797.
12. (l) Kabra, V.; Ojha, S.; Kaushik, P.; Meel, A. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 2337.
13. (a) Westheimer, F. H. Science 1987, 235, 1173.
14. (b) Catrina, I. E.; Hengge, A. C. J. Am. Chem. Soc. 1999, 121, 2156.
15. (c) Mol, C. D.; Izumi, T.; Mitra, S.; Tainer, J. A. Nature 2000, 403, 451.
16. (d) Holtz, K. M.; Catrina, I. E.; Hengge, A. C.; Kantrowitz, E. R. Biochemistry 2000, 39, 9451.
17. (e) Lahiri, S. D.; Zhang, G.; Dunaway-Mariano, D.; Allen, K. N. Science 2003, 299, 2067.
18. (f) Catrina, I. E.; Hengge, A. C. J. Am. Chem. Soc. 2003, 125, 7546.
19. (g) Hengge, A. C.; Onyido, I. Curr. Org. Chem. 2005, 9, 61.
20. (h) Onyido, I.; Swierczek, K.; Purcell, J.; Hengge, A. C. J. Am. Chem. Soc. 2005, 127, 7703.
21. (i) Um, I. H.; Shin, Y. H.; Han, J. Y.; Mishima, M. J. Org. Chem. 2006, 71, 7715.
22. (j) Kumara Swamy, K. C.; Satish Kumar, N. Acc. Chem. Res. 2006, 39, 324,
23. (k) van Bochove, M. A.; Swart, M.; Bickelhaupt, F. M. J. Am. Chem. Soc. 2006, 128, 10738.
24. (a) Cook, R. D.; Rahhal-Arabi, L. Tetrahedron Lett. 1985, 26, 3147.
25. (b) Cook, R. D.; Daouk, W. A.; Hajj, A. N.; Kabbani, A.; Kurku, A.; Samaha, M.; Shayban, F.; Tanielian, O. V. Can. J. Chem. 1986, 64, 213.
26. (c) Friedman, J. M.; Freeman, S.; Knowles, J. R. J. Am. Chem. Soc. 1988, 110, 1268.
27. (d) Hoff, R. H.; Hengge, A. C. J. Org. Chem. 1998, 63, 6680.
28. (e) Admiraal, S. J.; Herschlag, D. J. Am. Chem. Soc. 2000, 122, 2145.
29. (f) Harger, M. J. P. J. Chem. Soc., Perkin Trans. 2 2002, 489.
30. (g) Harger, M. J. P. Chem. Commun. 2005, 22, 2863.
31. (h) Hengge, A. C. Adv. Phys. Org. Chem. 2005, 40, 49.
32. (i) Sorensen-Stowell, K.; Hengge, A. C. J. Org. Chem. 2006, 71, 7180.
33. P=0 system: (a) Reimschüssel, W.; Mikolajczyk, M.; Slebocka-Tilk, H.; Gajl, M. Int. J. Chem. Kinet. 1980, 12, 979.
34. (b) Istomin, B. I.; Eliseeva, G. D. J. Gen. Chem. USSR (Engl. Transl.) 1981, 51, 2063.
35. (c) Bourne, N.; Chrystiuk, E.; Davis, A. M.; Williams, A. J. Am. Chem. Soc. 1988, 110, 1890.
36. (d) Humphry, T.; Forconi, M.; Williams, N. H.; Hengge, A. C. J. Am. Chem. Soc. 2004, 126, 11864.
37. P=S system: (a) Eliseeva, G. D.; Istomin, B. I.; Kalabina, A. V. J. Gen. Chem. USSR (Engl. Transl.) 1979, 49, 1912.
38. (b) Istomin, B. I.; Voronkov, M. G.; Zhdankovich, E. L.; Bazhenov, B. N. Dokl. Phys. Chem. (Engl. Transl.) 1981, 258, 659.
39. (c) Omakor, J. E.; Onyido, I.; vanLoon, G. W.; Buncel, E. J. Chem. Soc., Perkin Trans. 2 2001, 324.
40. (a) Pavan Kumar, K. V. P.; Praveen Kumar, K.; Vijjulatha, M.; Kumara Swamy, K. C. J. Chem. Sci. 2004, 116, 311.
41. (b) Vijjulatha, M.; Praveen Kumar, K.; Kumara Swamy, K. C.; Vittal, J. J. Tetrahedron Lett. 1998, 39, 1819.
42. (c) Silverberg, L. J.; Dillon, J. L.; Purushotham, V. Tetrahedron Lett. 1996, 37, 771.
43. (d) Corriu, R. J. P.; Lanneau, G. F. Leclercq, D. Tetrahedron 1989, 45, 1959.
44. (e) Corriu, R. J. P.; Lanneau, G. F.; Leclercq, D. Tetrahedron 1986, 42, 5591.
45. (a) Guha, A. K.; Lee, H. W.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1999, 765.
46. (b) Guha, A. K.; Lee, H. W.; Lee, I. J. Org. Chem. 2000, 65, 12.
47. (c) Lee, H. W.; Guha, A. K.; Lee, I. Int. J. Chem. Kinet. 2002, 34, 632.
48. (d) Lee, H. W.; Guha, A. K.; Kim, C. K.; Lee, I. J. Org. Chem. 2002, 67, 2215.
49. (e) Adhikary, K. K.; Lee, H. W.; Lee, I. Bull. Korean Chem. Soc. 2003, 24, 1135.
50. (a) Lee, I. Chem. Soc. Rev. 1990, 19, 317.
51. (b) Lee, I. Adv. Phys. Org. Chem. 1992, 27, 57.
52. (c) Lee, I.; Lee, H. W. Collect. Czech. Chem. Commun. 1999, 64, 1529.
53. (a) Oivanen, M.; Ora, M.; Lonnberg, H. Collect. Czech. Chem. Commun. 1996, 61, S-1.
54. (b) Hondal, R. J.; Bruzik, K. S.; Zhao, Z.; Tsai, M. D. J. Am. Chem. Soc. 1997, 119, 5477.
55. (c) Gregersen, B. A.; Lopez, X.; York, D. M. J. Am. Chem. Soc. 2003, 125, 7178.
56. (d) Liu, Y.; Gregersen, B. A.; Hengge, A. C.; York, D. M. Biochemistry 2006, 45, 10043.
57. Lee, I. Chem. Soc. Rev. 1995, 24, 223.
58. Hehre, W. J.; Random, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; Chapter 4.
59. (a) Lee, I.; Shim, C. S.; Chung, S. Y.; Lee, H. W. J. Chem. Soc., Perkin Trans. 2 1988, 975.
60. (b) Lee, I.; Kim, I. C. Bull. Korean Chem. Soc. 1988, 9, 133.
61. (c) Lee, I.; Shim, C. S.; Chung, S. Y.; Kim, H. Y.; Lee, H. W. J. Chem. Soc., Perkin Trans. 2 1988, 1919.
62. (d) Lee, I.; Shim, C. S.; Lee, H. W. J. Phys. Org. Chem. 1989, 2, 484.
63. (e) Lee, I.; Hong, S. W.; Park, J. H. Bull. Korean Chem. Soc. 1989, 10, 459.
64. (f) Lee, I.; Shim, C. S.; Lee, H. W. J. Chem. Res. 1992, (S) 90-91, (M) 0769-0793.
65. (g) Lee, B. C.; Yoon, J. H.; Lee, C. G.; Lee, I. J. Phys. Org. Chem. 1994, 7, 273.
66. (h) Oh, H. K.; Shin, C. H.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1995, 1169.
67. (i) Koh, H. J.; Lee, H. C.; Lee, H. W.; Lee, I. Bull. Korean Chem. Soc. 1995, 16, 839.
68. (j) Koh, H. J.; Lee, O. S.; Lee, H. W.; Lee, I. J. Phys. Org. Chem. 1997, 10, 725.
69. (k) Koh, H. J.; Han, K. L.; Lee, H. W.; Lee, I. J. Org. Chem. 2000, 65, 4706.
70. (l) Lee, K. S.; Adhikary, K. K.; Lee, H. W.; Lee, B. S.; Lee, I. Org. Biomol. Chem. 2003, 1, 1989.
71. (m) Lee, I.; Lee, H. W.; Yu, Y. K. Bull. Korean Chem. Soc. 2003, 24, 993.
72. (a) Lee, I.; Kim, H. Y.; Kang, H. K.; Lee, H. W. J. Org. Chem. 1988, 53, 2678.
73. (b) Lee, I.; Koh, H. J.; Lee, B. S.; Lee, H. W. J. Chem. Soc., Chem. Commun. 1990, 335.
74. Lee, I.; Shim, C. S.; Lee, H. W.; Lee, B. S. Bull. Korean Chem. Soc. 1991, 12, 255.
75. One of the reviewers indicated the possible TS of 6 with hydrogen bonding involving the strong acceptor P=O. The proposed TS cannot be completely excluded, and further work on phosphinates will clarify the TS structure. (Chemical Equation Presented)
76. (a) Head-Gordon, M.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1988, 153, 503.
77. (b) Head-Gordon, M.; Pople, J. A. J. Chem. Phys. 1988, 89, 5777.
78. (c) Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 275.
79. (d) Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 281.
80. (e) Head-Gordon, M.; Head-Gordon, T. Chem. Phys. Lett. 1994, 220, 122.
81. (a) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.
82. (b) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669.
83. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
84. (b) Carpenter, J. E.; Weinhold, F. J. Mol. Struct.: THEOCHEM 1988, 169, 41.
85. (c) Glendening, E. D.; Weinhold, F. J. Comput. Chem. 1998, 19, 593.
86. (d) Glendening, E. D.; Weinhold, F. J. Comput. Chem. 1998, 19, 610.
87. (e) Glendening, E. D.; Badenhoop, J. K.; Weinhold, F. J. Comput. Chem. 1998, 19, 628.
88. The specific solvation effects are calculated by a simple supermolecular approach adding one acetonitrile molecule at the fixed TS geometries.
89. Lee, I.; Lee, H. W.; Sohn, S. C.; Kim, C. H. Tetrahedron 1985, 41, 2635.