Oxidation of pinacyanol chloride by H2O2 catalyzed by FeIII complexed to tetraamidomacrocyclic ligand: Unusual kinetics and product identification

Journal of Coordination Chemistry

Volumn 63, Issue 14-16, 2010, Pages 2605-2618

  Mitchell, Douglas A ^a,b   Ryabov, Alexander D ^a   Kundu, Soumen ^a   Chanda, Arani ^a,c   Collins, Terrence J ^a  

^a CARNEGIE MELLON UNIVERSITY   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^c EISAI INC   (United States)

Author keywords

Hydrogen peroxide; Iron TAML complexes; Kinetics; Oxidation; Pinacyanol chloride

Indexed keywords

EID: 77955876423     PISSN: 00958972     EISSN: 10290389     Source Type: Journal    
DOI: 10.1080/00958972.2010.492426     Document Type: Article

References (44)

1. T.J. Collins. Acc. Chem. Res., 27, 279 (1994).
2. T.J. Collins. Acc. Chem. Res., 35, 782 (2002).
3. T.J. Collins, C. Walter. Sci. Am., 294, 83-88, 90 (2006).
4. A. Ghosh, A.D. Ryabov, S.M. Mayer, D.C. Horner, D.E. Prasuhn Jr, S. Sen Gupta, L. Vuocolo, C. Culver, M.P. Hendrich, C.E.F. Rickard, R.E. Norman, C.P. Horwitz, T.J. Collins. J. Am. Chem. Soc., 125, 12378 (2003).
5. A. Ghosh, D.A. Mitchell, A. Chanda, A.D. Ryabov, D.L. Popescu, E. Upham, G.J. Collins, T.J. Collins. J. Am. Chem. Soc., 130, 15116 (2008).
6. T.J. Collins, S.K. Khetan, A.D. Ryabov. In Chemistry and Applications of Iron-TAML Catalysts in Green Oxidation Processes Based on Hydrogen Peroxide, P.T. Anastas, R.H. Crabtree (Eds), pp. 39-77, Wiley-VCH Verlag GmbH & KgaA, Weinheim (2009).
7. N. Chahbane, D.-L. Popescu, D.A. Mitchell, A. Chanda, D. Lenoir, A.D. Ryabov, K.-W. Schramm, T.J. Collins. Green Chem., 9, 49 (2007).
8. A. Chanda, A.D. Ryabov, S. Mondal, L. Alexandrova, A. Ghosh, Y. Hangun-Balkir, C.P. Horwitz, T.J. Collins. Chem. Eur. J., 12, 9336 (2006).
9. C.P. Horwitz, D.R. Fooksman, L.D. Vuocolo, S.W. Gordon-Wylie, N.J. Cox, T.J. Collins. J. Am. Chem. Soc., 120, 4867 (1998).
10. A. Cornish-Bowden. Fundamentals of Enzyme Kinetics, Portland Press, London (1995).
11. A. Fersht. Structure and Mechanism in Protein Science: A Guide to Enzyme Catalysis and Protein Folding, Freeman, NY (1999).
12. M. Dequaire, B. Limoges, J. Moiroux, J.-M. Saveant. J. Am. Chem. Soc., 124, 240 (2002).
13. A.N. Shevelkova, Y.I. Sal'nikov, N.L. Kuzmina, A.D. Ryabov. FEBS Lett., 383, 259 (1996).
14. A.D. Ryabov, T.J. Collins. Adv. Inorg. Chem., 61, 471 (2009).
15. A. Theodoridis, J. Maigut, R. Puchta, E.V. Kudrik, R. van Eldik. Inorg. Chem., 47, 2994 (2008).
16. A. Mishra, R.K. Behera, P.K. Behera, B.K. Mishra, G.B. Behera. Chem. Rev., 100, 1973 (2000).
17. B.A. Armitage. Top. Curr. Chem., 253, 55 (2005).
18. R.G. Bhirud, E.V. Srisankar, K.S. Narayan. Proc. Indian Acad. Sci., Chem. Sci., 103, 83 (1991).
19. M.H. Robbins, R.S. Drago. J. Catal., 170, 295 (1997).
20. S.R. Segal, S.L. Suib, L. Foland. Chem. Mater., 9, 2526 (1997).
21. T. Yamada, S. Shinoda, K. Kikawa, A. Ichimura, J. Teraoka, T. Takui, H. Tsukube. Inorg. Chem., 39, 3049 (2000).
22. P.H. Roos, N. Jakubowski. Anal. Bioanal. Chem., 392, 1015 (2008).
23. U.M. Zanger, M. Turpeinen, K. Klein, M. Schwab. Anal. Bioanal. Chem., 392, 1093 (2008) Available online at: www.chem.cmu.edu/groups/collins/ awardpatpub/patents/index.html.
24. V.N. Goral, M.I. Nelen, A.D. Ryabov. Anal. Lett., 28, 2139 (1995).
25. L.D. Derkacheva. Izv. Akad. Nauk SSSR, Ser. Fiz., 20, 410 (1956).
26. W. West, S. Perace. J. Phys. Chem., 69, 1894 (1965).
27. R. Sabate, J. Estelrich. Spectrochim. Acta A Mol. Biomol. Spectrosc., 70, 471 (2008).
28. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J. Montgomery, J.A.T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03 (release B.05), Gaussian, Inc., Wallingford CT (2004).
29. R.G. Parr, W. Yang. Density-functional Theory of Atoms and Molecules, Clarendon, NY (1989).
30. T. Ziegler. Chem. Rev., 91, 651 (1991).
31. A.D. Becke. J. Chem. Phys., 98, 5648 (1993).
32. C. Lee, W. Yang, R.G. Parr. Phys. Rev. B: Condens. Matter, 37, 785 (1988).
33. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, M.J. Frisch. J. Phys. Chem., 98, 11623 (1994).
34. S. Barazzouk, H. Lee, S. Hotchandani, P.V. Kamat. J. Phys. Chem. B, 104, 3616 (2000).
35. D.-L. Popescu, A. Chanda, M.J. Stadler, S. Mondal, J. Tehranchi, A.D. Ryabov, T.J. Collins. J. Am. Chem. Soc., 130, 12260 (2008).
36. A. Chanda, X. Shan, M. Chakrabarti, W. Ellis, D. Popescu, F. Tiago de Oliveria, D. Wang, L. Que Jr, T.J. Collins, E. Munck, E.L. Bominaar. Inorg. Chem., 47, 3669 (2008).
37. F. Tiago de Oliveira, A. Chanda, D. Banerjee, X. Shan, S. Mondal, L. Que Jr, E.L. Bominaar, E. Munck, T.J. Collins. Science, 315, 835 (2007).
38. C.W. Jones. Applications of Hydrogen Peroxide and Derivatives, The Royal Society of Chemistry, Cambridge (1999).
39. R. van Eldik. Inorganic High Pressure Chemistry. Kinetics and Mechanisms, Vol.7, Elsevier, NY (1986).
40. V. Polshin, D.-L. Popescu, A. Fischer, A. Chanda, D.C. Horner, E.S. Beach, J. Henry, Y.-L. Qian, C.P. Horwitz, G. Lente, I. Fabian, E. Munck, E.L. Bominaar, A.D. Ryabov, T.J. Collins. J. Am. Chem. Soc., 130, 4497 (2008).
41. K.I. Pokrovskaya, I.I. Levkoev, S.V. Natanson. Zh. Fiz. Khim., 30, 161 (1956)
42. E.V. Vasil'eva. Zh. Anal. Khim., 2, 167 (1947).
43. A.K. Babko, E.V. Vasileva. Zh. Anal. Khim., 2, 159 (1947).
44. P.P. Turov, D.S. Turova. Zh. Anal. Khim., 25, 934 (1970).