Kinetics of cleavage of thiophosphates and phosphonothioates by micellar iodosocarboxylates and copper metallomicelles

Langmuir

Volumn 16, Issue 16, 2000, Pages 6485-6491

  Moss, Robert A ^a   Morales Rojas, Hugo ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGENTS; CATALYSIS; HYDROLYSIS; OXIDATION; PH EFFECTS; REACTION KINETICS; TOXIC MATERIALS;

CLEAVAGE; COPPER METALLOMICELLES; MICELLAR IODOSOCARBOXYLATES; PHOSPHONOTHIOATES; THIOPHOSPHATES;

MICELLES;

EID: 0034248581     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la000462q     Document Type: Article

References (43)

1. (a) Moss, R. A.; Kotchevar, A. T.; Park, B. D.; Scrimin, P. Langmuir 1996, 12, 2200.
2. (b) Moss, R. A.; Kim, K. Y.; Swarup, S. J. Am. Chem. Soc. 1986, 108, 788.
3. (c) Moss, R. A.; Alwis, K. W.; Shin, J.-S. J. Am. Chem. Soc. 1984, 106, 2651.
4. (d) Moss, R. A.; Alwis, K. W.; Bizzigotti, G. O. J. Am. Chem. Soc. 1983, 105, 681.
5. (e) Katriztky, A. R.; Duell, B. L.; Durst, H. D.; Knier, B. L. J. Org. Chem. 1988, 53, 3972.
6. Bunton, C. A.; Robinson, L. J. Org. Chem. 1969, 34, 773. Note: PNP is used to represent p-nitrophenyl throughout this report.
7. Hammond, P. S.; Forster, J. S.; Lieske, C. N.; Durst, H. D. J. Am. Chem. Soc. 1989, 111, 7860.
8. (a) Yang, Y.-C. Acc. Chem. Res. 1999, 32, 109.
9. (b) Yang, Y.-C. Chem. Ind. (London) 1995, 334.
10. (c) Yang, Y.-C.; Baker, J. A.; Ward, J. R. Chem. Rev. 1992, 92, 1729.
11. Epstein, J.; Callahan, J.-J.; Bauer, V. E. Phosphorus 1974, 4, 157.
12. Yang, Y.-C.; Szafraniec, L. L.; Beaudry, W. T.; Rohrbaugh, D. K. J. Am. Chem. Soc. 1990, 112, 6621.
13. (a) Yang, Y.-C.; Szafraniec, L. L.; Beaudry, W. T.; Bunton, C. A. J. Org. Chem. 1993, 58, 6964.
14. (b) Yang, Y.-C.; Berg, F. J.; Szafreniec, L. L.; Beaudry, W. T.; Bunton, C. A.; Kumar, A. J. Chem. Soc., Perkin Trans. 2 1997, 607.
15. Yang, Y.-C.; Szafraniec, L. L.; Beaudry, W. T.; Rohrbaugh, D. K.; Procell, L. R.; Samuel, J. B. J. Org. Chem. 1996, 61, 8407.
16. Berg, F. J.; Moss, R. A.; Yang, Y.-C.; Zhang, H. Langmuir 1995, 11, 411.
17. 11
18. Bunton, C. A.; Foroudian, H. J.; Gillitt, N. D. J. Phys. Org. Chem. 1999, 12, 758.
19. Blasko, A.; Bunton, C. A.; Hong, Y. S.; Mhala, M. M.; Moffatt, J. R.; Wright, S. J. Phys. Org. Chem. 1991, 4, 618.
20. Blasko, A.; Bunton, C. A.; Kumar, A. J. Phys. Org. Chem. 1997, 10, 427.
21. Scrimin, P.; Ghirlanda, G.; Tecilla, P.; Moss, R. A. Langmuir 1996, 12, 6235.
22. The tetradecyl analogue of 14 was first introduced as a hydrolytic catalyst by: Menger, F. M.; Gan, L. H.; Johnson, E.; Durst, H. D. J. Am. Chem. Soc. 1987, 109, 2800.
23. The reaction conditions are those defined for EPN, above.
24. 4.
25. In analogy to the parallel reaction with 11. Cf.: Lewis, V. E.; Donarski, W. J.; Wild, J. R.; Raushel, F. M. Biochemistry 1988, 27, 1591.
26. -1 at [(CTA)Cl] = 5 mM. See Table 1 for comparisons to IBA or INA.
27. Scrimin P. in Supramolecular Control of Structure and Reactivity; Hamilton, A. D., Ed.; Wiley: New York, 1996; p 101 f.
28. -1.
29. KOH hydrolysis of 10 also generates 17 visible at δ 55.6.
30. 2P(=S)Cl. Reaction of 17, under the conditions employed for parathion, afforded the products with signals at δ 6.8, 1.53, 1.37, and 0.08, previously obtained from the parathion.
31. 3: Michalski, J.; Mlotkowska, B. M.; Skowronska, A. J. Chem. Soc., Perkin Trans. 1 1974, 319.
32. With a 2.5:1 excess of 10 relative to INA, a stoichiometric cleavage would proceed to 40%.
33. (a) Moss, R. A.; Scrimin, P.; Rosen, R. T. Tetrahedron Lett. 1987, 28, 251.
34. (b) Moss, R. A.; Zhang, H. J. Am. Chem. Soc. 1994, 116, 4471.
35. Cook, R. D.; Farah, S.; Ghawi, L.; Itani, A.; Rahil, J. Can. J. Chem. 1986, 64, 1630.
36. Ketelar, J. A. A.; Gersmann, H. R.; Beck, M. M. Nature 1956, 177, 392.
37. Larson, R. A.; Weber, E. J. Reaction Mechanisms in Environmental Organic Chemistry; CRC Press: New York, 1994; p 147.
38. Kayima, M.; Mitsuhashi, S.; Makino, M. Chemosphere 1992, 25, 1783.
39. Eto, M., Ed. Organophosphorus Pesticides: Organic and Biological Chemistry; CRC Press: New York, 1974; p 58.
40. Blasko, A.; Bunton, C. A.; Foroudian, H. J. J. Colloid Interface Sci. 1994, 163, 500.
41. Moss, R. A.; Zhang, H.; Chatterjee, S.; Krogh-Jespersen, K. Tetrahedron Lett. 1993, 34, 1729.
42. Corriu, R. J. P.; Lanneau, G. F.; Leclercq, D. Tetrahedron 1980, 36, 1617.
43. De Bruin, K. E.; Tang, C.-I.; Johnson, D. M.; Wilde, R. L. J. Am. Chem. Soc. 1989, 111, 5871.