Epoxidation of Alkenes with H2O2 Catalyzed by Dititanium-Containing 19-Tungstodiarsenate(III): Experimental and Theoretical Studies

European Journal of Inorganic Chemistry

Volumn , Issue 33, 2010, Pages 5312-5317

  Donoeva, Baira G ^a   Trubitsina, Tatiana A ^a   Antonova, Nadya S ^b   Carbã, Jorge J ^b   Poblet, Josep M ^b   Al Kadamany, Ghada ^c   Kortz, Ulrich ^c   Kholdeeva, Oxana A ^a  

^a BORESKOV INSTITUTE OF CATALYSIS   (Russian Federation)

^b UNIVERSITAT ROVIRA I VIRGILI   (Spain)

^c JACOBS UNIVERSITY BREMEN   (Germany)

Author keywords

Density functional calculations; Epoxidation; Hydrogen peroxide; Polyoxometalates; Titanium

Indexed keywords

ATOMS; DENSITY FUNCTIONAL THEORY; MOLECULAR ORBITALS; OXYGEN; TITANIUM COMPOUNDS;

ALKENE SUBSTRATE; DENSITY-FUNCTIONAL CALCULATIONS; ELECTROPHILIC OXYGEN; HYDROPEROXO COMPLEX; OH-GROUPS; OXYGEN ATOM TRANSFER; POLYOXOMETALATES; REVERSIBLE INTERACTIONS; THEORETICAL STUDY; TITANIA;

HYDROCARBONS;

EID: 78649237658     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201000615     Document Type: Article

References (50)

1. G. Franz, R. A. Sheldon, in: Ulmann's Encyclopedia of Industrial Chemistry, 5th ed., vol. A (18), VCH Verlagsgesellschaft, Weinheim (Germany), 1991, pp. 261-311.
2. K. A. Jorgensen, Chem. Rev. 1989, 89, 432-458.
3. M. Dusi, T. Mallat, A. Baiker, Catal. Rev. Sci. Eng. 2000, 42, 213-278.
4. B. S. Lane, K. Burgess, Chem. Rev. 2003, 103, 2457-2473.
5. R. A. Sheldon, M. C. A. van Vliet, in: Fine Chemicals through Heterogeneous Catalysis (Eds.:, R. A. Sheldon, H. van Bekkum), Wiley, Weinheim, 2001, pp. 473-490.
6. Catalytic Oxidations with Hydrogen Peroxide as Oxidant (Ed.:, G. Strukul), Kluwer Academic, Dordrecht, The Netherlands, 1992.
7. C. W. Jones, Application of Hydrogen Peroxide and Derivatives, Royal Chemical Society of Chemistry, Cambridge (UK), 1999.
8. G. Centi, S. Perathoner, S. Abate, in: Modern Heterogeneous Oxidation Catalysis: Design, Reactions and Characterization (Ed.:, N. Mizuno), Wiley-VCH, Weinheim (Germany), 2009, pp. 253-288.
9. B. Notari, Adv. Catal. 1996, 41, 253-334.
10. J. M. Thomas, R. Raja, Top. Catal. 2006, 40, 3-17.
11. P. Ratnasamy, D. Srinivas, H. Knozinger, Adv. Catal. 2004, 48, 1-169.
12. O. A. Kholdeeva, N. N. Trukhan, Russ. Chem. Rev. 2006, 75, 411-432.
13. M. Taramasso, G. Perego, B. Notari, US Patent 4,410,501 (1983).
14. M. G. Clerici, Top. Catal. 2000, 13, 373-386.
15. C. Perego, A. Carati, P. Ingalina, M. A. Mantegazza, G. Bellussi, Appl. Catal. A 2001, 221, 63-72.
16. F. Cavani, A. M. Gaffney, in: Sustainable Industrial Processes (Eds.:, F. Cavani, G. Centi, S. Perathoner, F. TrifirÃ), Wiley-VCH, Weinheim (Germany), 2009.
17. E. A. Quadrelli, J.-M. Basset, Coord. Chem. Rev. 2010, 254, 707-728.
18. O. A. Kholdeeva, Top. Catal. 2006, 40, 229-243.
19. O. A. Kholdeeva, R. I. Maksimovskaya, J. Mol. Catal. A 2007, 262, 7-24.
20. O. A. Kholdeeva, G. M. Maksimov, R. I. Maksimovskaya, L. A. Kovaleva, M. A. Fedotov, V. A. Grigoriev, C. L. Hill, Inorg. Chem. 2000, 39, 3828-3837.
21. O. A. Kholdeeva, T. A. Trubitsina, R. I. Maksimovskaya, A. V. Golovin, W. A. Neiwert, B. A. Kolesov, X. LÃpez, J.-M. Poblet, Inorg. Chem. 2004, 43, 2284-2292.
22. O. A. Kholdeeva, T. A. Trubitsina, G. M. Maksimov, A. V. Golovin, R. I. Maksimovskaya, Inorg. Chem. 2005, 44, 1635-1642.
23. O. A. Kholdeeva, L. A. Kovaleva, R. I. Maksimovskaya, G. M. Maksimov, J. Mol. Catal. A 2000, 223-229.
24. F. Hussain, B. S. Bassil, U. Kortz, O. A. Kholdeeva, M. N. Timofeeva, P. de Oliveira, B. Keita, L. Nadjo, Chem. Eur. J. 2007, 13, 4733-4742.
25. O. A. Kholdeeva, B. G. Donoeva, T. A. Trubitsina, G. Al-Kadamany, U. Kortz, Eur. J. Inorg. Chem. 2009, 5134-5141.
26. R. Neumann, Prog. Inorg. Chem. 1998, 47, 317-370.
27. R. Neumann, Polyoxometalates as Catalysts for Oxidation with Hydrogen Peroxide and Molecular Oxygen, in: Transition Metals for Organic Synthesis, 2nd ed. (Eds.:, M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004, vol. 2, pp. 415-426.
28. N. S. Antonova, J. J. CarbÃ, U. Kortz, O. A. Kholdeeva, J. M. Poblet, J. Am. Chem. Soc. 2010, 132, 7488-7497.
29. D. V. Deubel, G. Frenking, P. Gisdakis, W. A. Herrmann, N. Rösch, J. Sundemeyer, Acc. Chem. Res. 2004, 37, 645-652, and references cited therein.
30. There are several examples of the use of QM/MM methods as an analytical tool to separate and quantify the steric and electronic effect. For a couple of our own references, see for example
31. E. Bustelo, J. J. CarbÃ, A. LledÃs, K. Mereiter, M. C. Puerta, P. Valerga, J. Am. Chem. Soc. 2003, 125, 3311-3321.
32. J. J. CarbÃ, N. MartÃnez-Espada, M. Mena, M. E. G. Mosquera, J.-M. Poblet, C. YÃlamos, Chem. Eur. J. 2009, 15, 11619-11631.
33. [15]).
34. J. J. CarbÃ, A. LledÃs, D. Vogt, C. Bo, Chem. Eur. J. 2006, 12, 1457-1467.
35. Y. Nakagawa, K. Kamata, M. Kotani, K. Yamaguchi, N. Mizuno, Angew. Chem. Int. Ed. 2005, 44, 5136.
36. Gaussian 03 (Revision B.03), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. R. 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, 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. G. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 2004.
37. E. D. Glendening, A. E. Reed, J. E. Carpernter, F. Weinhold, Gaussian 03, Gaussian Inc., Wallingford, CT (USA), 2004; NBO version 3.1.
38. C. Lee, C. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
39. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
40. P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.
41. M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. Defrees, J. A. Pople, J. Chem. Phys. 1982, 77, 3654-3665.
42. W. J. Hehre, R. Ditchfield, J. A. Pople, J. Chem. Phys. 1972, 56, 2257-2261.
43. P. C. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213-222.
44. F. Maseras, K. Morokuma, J. Comput. Chem. 1995, 16, 1170-1179.
45. S. Humbel, S. Sieber, K. Morokuma, J. Chem. Phys. 1996, 105, 1959-7967.
46. M. Svensson, S. Humbel, R. D. J. Froese, T. Matsubara, S. Sieber, K. Morokuma, J. Phys. Chem. 1996, 100, 19357-19363.
47. M. Svensson, S. Humbel, K. Morokuma, J. Chem. Phys. 1996, 105, 3654-3661.
48. S. Dapprich, I. KomÃromi, K. S. Byun, K. Morokuma, M. J. Frisch, THEOCHEM 1999, 462, 1-21.
49. A. K. RappÃ, C. J. Casewit, K. S. Colwell, W. A. Goddard III, W. M. Skiff, J. Am. Chem. Soc. 1992, 114, 10024-10035.
50. P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 270-283.