Mechanism and reactivity of alkane C-H bond dissociation on coordinatively unsaturated aluminum ions, determined by theoretical calculations

Journal of Physical Chemistry A

Volumn 106, Issue 8, 2002, Pages 1619-1626

  Fǎrcaşiu, Dan ^a   Lukinskas, Povilas ^a  

^a University of Pittsburgh   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN TRANSFER;

CATALYSTS; CHEMICAL ACTIVATION; CHEMICAL BONDS; CHEMISORPTION; CRYSTAL LATTICES; DEHYDROGENATION; DISCRETE FOURIER TRANSFORMS; DISSOCIATION; ION EXCHANGE; ZEOLITES;

PARAFFINS;

EID: 0037185933     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp013724l     Document Type: Article

References (101)

1. (a) Taylor, H.S.; Diamond, H. J. Am. Chem. Soc. 1935, 57, 1256.
2. (b) Lee, J.K.; Weller, S.W. Anal. Chem. 1958, 30, 1057.
3. (c) Hall, W.K.; Leftin, H.P.; Cheselske, F.J.; O'Reilly, D.E. J. Catal. 1963, 2, 506.
4. (d) Hall, W.K.; Lutinski, F.E. J. Catal. 1963, 2, 518.
5. (e) Carter, J.; Lucchesi, P.; Corneil, P.; Yates, D.J.C.; Sinfelt, J.H. J. Phys. Chem. 1965, 69, 3070.
6. (f) Garrett, B.R.T.; Rooney, J.J. J. Chem. Soc., Perkin Trans. 2 1974, 960.
7. For references, see: Yoshida, S. In Theoretical Aspects of Heterogeneous Catalysis; Moffat, J.B., Ed.; Van Nostrand Reinhold: New York, 1990; p 506.
8. (a) Haag, W.O.; Dessau, R.M. Proc. 8th Intl. Congr. Catal., Berlin 1984, vol. 2; Dechema: Frankfurt-am Main, 1984; p 305.
9. (b) Abbot, J.; Wojchechowski, B. Ind. Eng. Chem. Prod. Res. Dev. 1985, 24, 501.
10. (c) Giannetto, G.; Sansare, S.; Guisnet, M. J. Chem. Soc., Chem. Commun. 1986, 1302.
11. (d) Hail, W.K.; Lombardo, E.A.; Engelhardt, J. J. Catal. 1989, 115, 611.
12. (e) See the discussion in Fǎrcaşiu, D.; Lukinskas, P. Rev. Roumaine Chim. 1999, 44, 1091.
13. (a) van Santen, R.A.; Kramer, G.J. Chem. Rev. 1995, 95, 637.
14. (b) Kazansky, V.B.; Frash, M.V.; van Santen, R.A. Appl. Catal., A 1996, 146, 225.
15. (c) Rigby, A.M.; Kramer, G.J.; van Santen, R.A. J. Catal. 1997, 170, 1.
16. (d) Bates, S.P.; van Santen, R.A. Adv. Catal. 1998, 42, 1.
17. (e) Zygmunt, S.A.; Curtiss, L.A.; Iton, L.E. Abstracts, 16th Meeting of the North American Catalysis Society, Boston, MA, June 2, 1999, 119.
18. (f) Esteves, P.M.; Nascimento, N.A.C.; Mota, C.J.A. J. Phys. Chem. B 1999, 103, 10417.
19. Zelenovskii, V.M.; Zhidomirov, G.M.; Kazanskii, V.B. Zh. Fiz. Khim. 1984, 58, 1788.
20. (a) Senchenya, I.N.; Kazanskii, V.B. Kinet. I Katal. 1988, 29, 1331.
21. (b) Ioka, F.; Sakka, T.; Ogata, Y.; Iwasaki, M. Can. J. Chem. 1993, 71, 663.
22. (a) Fǎrcaşiu, D.; Lukinskas, P. J. Phys. Chem. A 1999, 103, 8483.
23. (b) Lukinskas, P.; Fǎrcaşiu, D. Appl. Catal. A 2001, 209, 193.
24. (a) Khoobiar, S. J. Phys. Chem. 1964, 68, 411.
25. (b) Robell, A.J.; Ballou, E.V.; Boudart, M. J. Phys. Chem. 1964, 68, 2748.
26. (c) Vannice, M.A.; Neikan, W.C. J. Catal. 1971, 20, 260.
27. (d) Levy, R.V.; Boudart, M. J. Catal. 1974, 32, 304.
28. (e) Fleisch, T.; Aberman, R. J. Catal. 1977, 50, 268.
29. (f) Conner, W.C., Jr.; Pajonk, G.M.; Teichner, S.J. Adv. Catal. 1986, 34, 1.
30. (g) Musso, J.C.; Parera, J.M. Appl. Catal. 1987, 30, 81.
31. (a) Coster, D.; Blumenfeld, A.L.; Fripiat, J.J. J. Phys. Chem. 1994, 98, 6201.
32. (b) Lee, M.-H.; Cheng, C.-F.; Heine, V.; Klinowski, J. Chem. Phys. Lett. 1997, 265, 673.
33. Preliminary communication: Fǎrcaşiu, D.; Lukinskas, P. Chem. Commun. 2001, 77.
34. Schwarz, K.; Nusterer, E.; Blöchl, P.E. Catal. Today 1999, 50, 501.
35. Saner, J.; Ugliengo, P.; Garrone, G.; Saunders, V.R. Chem. Rev. 1994, 94, 2095.
36. Shertukde, P.V.; Hall, W.K.; Marcelin, G. Catal. Today 1992, 94, 491.
37. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Zakrzewski, V.G.; Montgomery, J.A., Jr.; Stratmann, R.E.; Burant, J.C.; Dapprich, S.; Millam, J.M.; Daniels, A.D.; Kudin, K.N.; Strain, M.C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G.A.; Ayala, P.Y.; Cui, Q.; Morokuma, K.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Cioslowski, J.; Ortiz, J.V.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P.M. W.; Johnson, B.G.; Chen, W.; Wong, M.W.; Andres, J.L.; Head-Gordon, M.; Replogle, E.S.; Pople, J.A. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1999.
38. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Gill, P.M.W.; Johnson, B.G.; Robb, M.A.; Cheeseman, J.R.; Keith, T.; Petersson, G.A.; Montgomery, J.A.; Raghavachari, K.; Al-Laham, M.A.; Zakrzewski, V.G.; Ortiz, J.V.; Foresman, J.B.; Cioslowski, J.; Stefanov, B.B.; Nanayakkara, A.; Challacombe, M.; Peng, C.Y.; Ayala, P.Y.; Chen, W.; Wong, M.W.; Andres, J.L.; Replogle, E.S.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Binkley, J.S.; Defrees, D.J.; Baker, J.; Stewart, J.P.; Head-Gordon, M.; Gonzalez, C.; Pople, J.A. Gaussian 94, revision D.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
39. (a) Pople, J.A. Acc. Chem. Res. 1970, 3, 217.
40. (b) Pople, J.A. Int. J. Mass Spectrom. Ion Phys. 1976, 19, 89.
41. (c) Hehre, W.J.; Radom, L.; Schleyer, P.v.R.; Pople, J.A. Ab initio Molecular Orbital Theory; Wiley-Interscience: New York, 1986.
42. (a) Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864.
43. (b) Kohn, W.; Sham, L. Phys. Rev. 1965, 140, Al133.
44. (c) Parr, R.G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
45. (d) Becke, A.D. J. Chem. Phys. 1993, 98, 5648.
46. Peng, C.; Schlegel, H.B. Isr. J. Chem. 1993, 33, 449.
47. Gonzales, C.; Schlegel, H.B. J. Phys. Chem. 1989, 90, 2154.
48. Chalasiňski, G.; Gutowski, M. Chem. Rev. 1988, 88, 943.
49. Schaftenaar, G. MOLDEN. A Portable Electron Density Program Available at: ftp ftp.caos.kun.nl. Name: anonymous.
50. XMol, version 1.3.1; Minnesota Supercomputing Center, Inc.: Minneapolis, MN, 1993.
51. Knözinger, H.; Ratnasamy, P. Catal. Rev. Sci. Eng. 1978, 17, 31.
52. 1 cal = 4.184 J.
53. (a) Holm, V.C.F.; Blue, R.W. Ind. Eng. Chem. 1951, 43, 501.
54. (b) Carleton, F.B.; Gilmore, T.A.; Laverty, T.D.; Rooney, J.J. J. Chem. Soc. Chem. Commun. 1977, 896.
55. (c) Narbershuber, T.F.; Vinnek, H.; Lercher, J.A. J. Catal. 1995, 157, 388.
56. (d) Narbershuber, T.F.; Brait, T.; Seshan, K.; Lercher, J.A. J. Catal. 1997, 172, 127.
57. Frash, M.V.; van Santen, R.A. J. Phys. Chem. A 2000, 104, 2468.
58. Narbershuber, T.F.; Stockenhuber, M.; Brait, T.; Seshan, K.; Lercher, J.A. J. Catal. 1996, 160, 183.
59. Kazansky, V.B.; Borovkov, V. Yu.; Zaitsev, A.V. Proc. 9th Intl. Congr. Catal., Calgary 1988, 3, 1426.
60. Long, M.A.; Garnett, J.L.; Williams, P.G. Aust. J. Chem. 1982, 35, 1057.
61. (a) Schoofs, B.; Schuermans, J.; Schoonheydt, R.A. Micropor. Mesopor. Mater. 2000, 35-36, 99.
62. (b) Paravano, C.; Hammel, E.F.; Taylor, H.S. J. Am. Chem. Soc. 1948, 70, 2269.
63. (c) Hansford, R.C.; Waldo, P.G.; Drake, I.C.; Honig, R.E. Ind. Eng. Chem. 1952, 44, 1108.
64. (d) Hindin, S.G.; Mills, G.A.; Oblad, A.G. J. Am. Chem. Soc. 1955, 77, 538.
65. (e) Burwell, R.L., Jr.; Porte, H.A.; Hamilton, W.H. J. Am. Chem. Soc. 1959, 81, 828.
66. (f) Lapszewicz; J.A.; Jiang, X.-Z. Catal. Lett. 1992, 13, 103.
67. (g) Iglesia, E.; Baumgartner, J.E. Catal. Lett. 1993, 21, 545.
68. (h) Sommer, J.; Hachoumy, M.; Garin, F.; Barthomeuf, D. J. Am. Chem. Soc. 1994, 116, 5491.
69. (a) Bloch, H.S.; Pines, H.; Schmerling, L. J. Am. Chem. Soc. 1946, 68, 153.
70. (b) Nenitzescu, C.D.; Avram, M.; Sliam, E. Bull. Soc. Chem. France 1955, 1266.
71. (c) See also: Nenitzescu, C.D.; Cantuniari, I.P. Ber. Dtsch. Chem. Ges. 1933, 66, 1097.
72. (a) J.M.Oelderik cited in: Brouwer, D.M.; Mackor, E.L. Proc. Chem. Soc. 1964, 147.
73. (b) Oelderik, J.M.; Mackor, E.L.; Platteeuw, J.C.; van der Wie, A. British Patent 981,311 (appl. 1962), equivalent to U.S. Patent 3,201,494, 1965.
74. (c) Brouwer, D.M.; Hogeveen, H. Prog. Phys. Org. Chem. 1972, 9, 179.
75. Fǎrcaşiu, D.; Siskin, M.; Rhodes, R.P. J. Am. Chem. Soc. 1979, 101, 7671.
76. (a) Jacobs, P.A. Carboniogenic Activity of Zeolites; Elsevier: Amsterdam, 1977.
77. (b) Mirodatos, C.; Barthomeuf, D. J. Chem. Soc. Chem. Commun. 1981, 39.
78. (c) Jacobs, P.A. Catal. Rev.-Sci. Eng. 1982, 24, 415.
79. (d) Mihindou-Koumba, P.C.; Lemberton, J.L.; Perot, G.; Guisnet, M. Nouv. J. Chim. 1984, 8, 31.
80. (e) Patrilyak, K.I.; Bortyshevskii, V.A.; Tsuprik, I.N.; Gutyrya, V.S.; Baiburskii, V.L. Doklady Akademii Nauk S. S. S. R. 1985, 283, 384.
81. Martens, J.A.; Jacobs, P.A. In ref 2, p 52.
82. Treatments of alkene hydrogenation/alkane dehydrogenation: (a) Senger, S.; Radom., L. J. Am. Chem. Soc. 2000, 122, 2613.
83. (b) Kazansky, V.B.; Frash, M.V.; van Santen, R.A. Catal. Lett. 1994, 28, 211.
84. (a) Fǎrcaşiu, D.; Marino, G.M.; Kastrup, R.V.; Rose, K.D. presented at the 185th American Chemical Society National Meeting, Seattle, WA, March 1983, Abstract ORGN 160.
85. (b) Fǎrcaşiu, D.; Ghenciu, A.; Marino, G.; Rose, K.D. J. Am. Chem. Soc. 1997, 119, 11826.
86. (a) Fǎrcaşiu, D. J. Chem. Soc. Chem. Commun. 1994, 1801.
87. Xu, T.; Munson, E.J.; Haw, J.F. J. Am. Chem. Soc. 1994, 116, 1962.
88. (a) Fǎrcaşiu, D. Lukinskas, P. J. Chem. Soc., Perkin Trans. 2 1999, 1609.
89. (b) Fǎrcaşiu, D. Lukinskas, P. J. Chem. Soc., Perkin Trans. 2 1999, 2715.
90. (c) Fǎrcaşiu, D. Lukinskas, P. J. Chem. Soc., Perkin Trans. 2 2000, 2295.
91. Olah, G.A.; Surya Prakash, G.K.S.; Sommer, J. Superacids; Wiley: New York, 1985; p 249.
92. Sokolovskii, V.D.; Mamedov, E.A. Catal. Today 1992, 14, 331 (Part 4).
93. Capitán, M.J.; Odriozola, J.A.; Márquez, A.; Sanz, J.F. J. Catal. 1995, 156, 273.
94. (a) Stamires, D.N.; Turkevich, J. J. Am. Chem. Soc. 1964, 86, 749.
95. (b) Shih, S. J. Catal. 1983, 79, 390.
96. (c) McVicker, G.B.; Kramer, G.M.; Ziemiak, J.J. J. Caral. 1983, 83, 286.
97. (d) Fǎrcaşiu, D.; Ghenciu, A. Prepr. Div. Pet. Chem., Am. Chem. Soc. 1994, 39, 479.
98. (e) Fǎrcaşiu, D.; Ghenciu, A.; Li, J.Q. J. Catal. 1996, 158, 116.
99. Alvarez, L.J.; Blumenfeld, A.L.; Fripiat, J.J. J. Chem. Phys. 1998, 108, 1724.
100. Fǎrcaşiu, D.; Lee, K.-H. J. Mol. Catal., A 2000, 161, 213.
101. Fǎrcaşiu, D.; Lee, K.-H. Catal. Commun. 2001, 2, 5.