An immobilized ortho-palladated dimethylbenzylamine complex as an efficient catalyst for the methanolysis of phosphorothionate pesticides

Inorganic Chemistry

Volumn 48, Issue 3, 2009, Pages 1183-1191

  Mohamed, Mark F ^a   Neverov, Alexei A ^a   Brown, R Stan ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLAMINE DERIVATIVE; MALATHION; METHANOL; NITROGEN; PALLADIUM; PESTICIDE; PHOSPHOROTHIOIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION; SOLUTION AND SOLUBILITY;

BENZYLAMINES; CATALYSIS; MALATHION; METHANOL; METHYLATION; MOLECULAR STRUCTURE; NITROGEN; PALLADIUM; PESTICIDES; SOLUTIONS; THIOPHOSPHORIC ACID ESTERS;

EID: 60849113460     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic801382e     Document Type: Article

References (56)

1. (a) Toy, A.; Walsh, E. N. Phosphorus Chemistry in Everyday Living, 2nd ed.; American Chemical Society: Washington, DC, 1987; pp 18-20.
2. (b) Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley: New York, 2000.
3. (c) Gallo, M. A.; Lawryk, N. J. Organophosphorus Pesticides. The Handbook of Pesticide Toxicology; Academic Press: San Diego, CA, 1991.
4. (d) Chernier, P. J. Survey of Industrial Chemistry, 2nd ed.; VCH: New York, 1992; pp 389-417.
5. Hassall, K. A. The Biochemistry and Uses of Pesticides, 2nd ed.; VCH: Weinheim, 1990; pp 269-275.
6. Morales-Rojas, H.; Moss, R. S. Chem. Rev. 2002, 102, 2497.
7. Shimazu, M.; Chen, W.; Mulchandani, A. ACS Symp. Ser. 2004, 863, 25-36.
8. (a) Tsang, J. S.; Neverov, A. A.; Brown, R. S. J. Am. Chem. Soc. 2003, 125, 7602.
9. (b) Tsang, J. A. W.; Neverov, A. A.; Brown, R. S. Org. Biomol. Chem. 2004, 2, 3457.
10. Liu, T.; Neverov, A. A.; Tsang, J. S. W.; Brown, R. S. Org. Biomol. Chem. 2005, 3, 1525.
11. Lewis, R. E.; Neverov, A. A.; Brown, R. S. Org. Biomol. Chem. 2005, 3, 4082.
12. Melnychuk, S. A.; Neverov, A. A.; Brown, R. S. Angew. Chem., Int. Ed. 2006, 45, 1767.
13. For the designation of pH in non-aqueous solvents, we use the forms recommended by the IUPAC: Compendium of Analytical Nomenclature. Definitive Rules 1997, 3rd ed.; Blackwell: Oxford, UK, 1998.
14. Neverov, A. A.; Brown, R. S. Org. Biomol. Chem. 2004, 2, 2245.
15. Didier, B.; Mohamed, M. F.; Csaszar, E.; Colizza, K. G.; Neverov, A. A.; Brown, R. S. Can. J. Chem. 2008, 86, 1.
16. Menger, F. M.; Tsuno, T. J. Am. Chem. Soc. 1989, 111, 4903.
17. (a) Lu, Q.; Singh, A.; Deschamps, J. R.; Chang, E. L. Inorg. Chim. Acta 2000, 309, 82.
18. (b) Hartshorn, C. M.; Singh, A.; Chang, E. L. J. Mater. Chem. 2002, 12, 602.
19. (c) Hartshorn, C. M.; Deschamps, J. R.; Singh, A.; Chang, E. L. React. Funct. Polym. 2003, 55, 219.
20. (a) Srivatsan, S. G.; Verma, S. Chem.-Eur. J. 2001, 7, 828.
21. (b) Srivatsan, S. G.; Parvez, M.; Verma, S. Chem.-Eur. J. 2002, 8, 5184.
22. (c) Chandraskhar, V.; Athmoolan, A.; Srivatsan, S. G.; Shanmuga Sundaram, P.; Verma, S.; Steiner, A.; Zacchini, S.; Butcher, R. Inorg. Chem. 2002, 41, 5162.
23. (d) Srivatsan, S. G.; Verma, S. Chem. Commun. 2000b, 515.
24. Hanafy, A. I.; Lykourinou-Tibbs, V.; Bisht, K. S.; Ming, L.-J. Inorg. Chim. Acta 2005, 358, 1247.
25. spH in methanol is 8.38; see: Bosch, E.; Rived, F.; Rosés, M.; Sales, J. J. Chem. Soc., Perkin Trans. 1999, 2, 1953.
26. Various Pd and Pt N,N-dimethylbenzylamine metallocycles and related species and their use for the hydrolysis of sulfur-containing OP materials have been described prior to our work, (a) Ryabov, A. D.; Kazankov, G. M.; Kurzeev, S. A.; Samuleev, P. V.; Polyakov, V. A. Inorg. Chim. Acta 1998, 280, 57.
27. (b) Kurzeev, S. A.; Kazankov, G. M.; Ryabov, A. D. Inorg. Chim. Acta 2000, 305, 1.
28. (c) Kazankov, G. M.; Sergeeva, V. S.; Eftemenko, E. N.; Alexandrova, L.; Varfolomeev, S. D.; Ryabov, A. D. Angew. Chem., Int. Ed. 2000, 39, 3117.
29. (d) Kazankov, G. M.; Sergeeva, V. S.; Borisenko, A. A.; Zatsman, A. I.; Ryabov, A. D. Russ. Chem. Bull. Int. Ed. 2001, 50, 1844.
30. Recent reports by Gabbaï et al. have also found structurally similar palladacycle complexes to be effective catalysts for the hydrolysis of the phosphorothionate methyl parathion. (a) Kim, M.; Liu, Q.; Gabbaï F. P. Organometallics 2004, 23, 5560.
31. (b) Kim, M.; Picot, A.; Gabbaï, F. P. Inorg. Chem. 2006, 45, 5600.
32. -1.
33. Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217.
34. (a) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058.
35. (b) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531.
36. (c) McNamara, C. E.; King, F.; Bradley, M. Tetrahedron Lett. 2004, 45, 8239.
37. Lu, Z.-L.; Neverov, A. A.; Brown, R. S., unpublished data.
38. Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Scordia, V. J. M. J. Chem. Soc., Dalton Trans. 2005, 991.
39. Nowotny, M.; Hanefeld, U.; van Koningsveld, H.; Maschmeyer, T. Chem. Commun. 2000, 1877.
40. Bedford, R. B.; Cazin, C. S. J.; Hursthouse, M. B.; Light, M. E.; Pike, K. J.; Wimperis, S. J. Organomet. Chem. 2001, 633, 173.
41. (a) Baleizäo, C.; Corma, A.; Garcia, H.; Leyva, A. J. Org. Chem. 2004, 69, 439.
42. (b) Das, D.; Garcia, H.; Leyva, A. J. Catal. 2005, 229, 322.
43. (c) Corma, A.; Garcia, H.; Leyva, A. J. Catal. 2006, 240, 87.
44. spH in methanol, see: Gibson, G.; Neverov, A. A.; Brown, R. S. Can. J. Chem. 2003, 81, 495.
45. Chauvin, Y.; Commereuc, D.; Dawans, F. Prog. Polym. Sci. 1977, 5, 95.
46. Ryabov, A.; Polyakov, V. A.; Yatsimirsky, A. K. J. Chem. Soc., Perkin Trans. 2 1983, 1503.
47. Guyot, A. Pure Appl. Chem. 1988, 60, 365.
48. Corma, A.; Garcia, H. Top. Catal. 2008, 48, 8.
49. Hartshorn, C. M.; Singh, A.; Chang, E. L. J. Mater. Chem. 2002, 12, 602.
50. a values are spread over several pH units due to statistical effects and, more importantly, electrostatic effects.
51. -2 M) and catalyst, which can alter the solution properties. It is possible, however, that the diminution of rate is attributable to a saturation binding of substrate and catalyst.
52. (a) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345.
53. (b) Dijkstra, H. P.; Slagt, M. Q.; McDonald, A.; Kruithof, C. A.; Kreiter, R.; Mills, A. M.; Lutz, M.; Speck, A. L.; Klopper, W.; Van Klink, G. P. M.; Van Koten, G. J. Catal. 2005, 229, 322.
54. Bonner, M. R.; Coble, J.; Blair, A.; Beane Freeman, L. E.; Hoppin, J. A.; Sandler, D. P.; Alavanja, M. C. R. Am. J. Epidemiol. 2007, 166, 1023.
55. Greenhalg, R.; Shoolery, J. N. Anal. Chem. 1978, 50, 2039.
56. Smith, B.; March, J. Advanced Organic Chemistry, 5th ed.; Wiley Interscience: New York, 2001; pp 338-342 and references therein.