Isomer-selective thermal activation of methane in the gas phase by [HMO]+ and [M(OH)]+ (M=Ti and V)

Angewandte Chemie - International Edition

Volumn 52, Issue 23, 2013, Pages 6097-6101

  Kretschmer, Robert ^a,b   Schlangen, Maria ^a   Schwarz, Helmut ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

C H activation; gas phase reactions; ligand effects; metal complexes; oxidation states

Indexed keywords

C-H ACTIVATION; CH-BOND ACTIVATION; GAS-PHASE REACTIONS; GASPHASE; LIGAND EFFECT; OXIDATION STATE; THERMAL ACTIVATION;

ACTIVATION ANALYSIS; METAL COMPLEXES; PHASE INTERFACES; TITANIUM;

METHANE;

EID: 84878423583     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201300900     Document Type: Article

References (105)

1. B. L. Conley, W. J. Tenn, K. J. H. Young, S. Ganesh, S. Meier, V. Ziatdinov, O. Mironov, J. Oxgaard, J. Gonzales, W. A. Goddard, R. A. Periana, Methane Functionalization, Wiley-VCH, Weinheim, 2006
2. W. B. Tolman, Activation of Small Molecules: Organometallic and Bioinorganic Perspectives, Wiley-VCH, Weinheim, 2006.
3. J. R. Webb, T. Bolano, T. B. Gunnoe, ChemSusChem 2011, 4, 37-49
4. G. A. Olah, A. Goeppert, G. K. S. Prakash, Beyond Oil and Gas: The Methanol Economy, Wiley-VCH, Weinheim, 2009
5. G. A. Olah, Angew. Chem. 2013, 125, 112-116
6. Angew. Chem. Int. Ed. 2013, 52, 104-107.
7. A. E. Shilov, G. B. Shul′pin, Chem. Rev. 1997, 97, 2879-2932
8. S. S. Stahl, J. A. Labinger, J. E. Bercaw, Angew. Chem. 1998, 110, 2298-2311
9. Angew. Chem. Int. Ed. 1998, 37, 2180-2192
10. C. G. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639
11. J. A. Labinger, J. E. Bercaw, Nature 2002, 417, 507-514
12. R. H. Crabtree, J. Organomet. Chem. 2004, 689, 4083-4091
13. K. Godula, D. Sames, Science 2006, 312, 67-72
14. R. G. Bergman, Nature 2007, 446, 391-393
15. H. M. L. Davies, J. R. Manning, Nature 2008, 451, 417-424
16. Y. Boutadla, D. L. Davies, S. A. Macgregor, A. I. Poblador-Bahamonde, Dalton Trans. 2009, 5820-5831
17. G. B. Shul'pin, Org. Biomol. Chem. 2010, 8, 4217-4228
18. T. Newhouse, P. S. Baran, Angew. Chem. 2011, 123, 3422-3435
19. Angew. Chem. Int. Ed. 2011, 50, 3362-3374.
20. K. Eller, H. Schwarz, Chem. Rev. 1991, 91, 1121-1177
21. D. K. Böhme, H. Schwarz, Angew. Chem. 2005, 117, 2388-2406
22. Angew. Chem. Int. Ed. 2005, 44, 2336-2354
23. D. K. Böhme, Can. J. Chem. 2008, 86, 177-198
24. G. E. Johnson, E. C. Tyo, A. W. Castleman, Jr., Proc. Natl. Acad. Sci. USA 2008, 105, 18108-18113
25. J. Roithová, D. Schröder, Coord. Chem. Rev. 2009, 253, 666-677
26. M. Schlangen, H. Schwarz, Dalton Trans. 2009, 10155-10165
27. J. Roithová, D. Schröder, Chem. Rev. 2010, 110, 1170-1211
28. H. Schwarz, Angew. Chem. 2011, 123, 10276-10297
29. Angew. Chem. Int. Ed. 2011, 50, 10096-10115
30. R. Kretschmer, M. Schlangen, H. Schwarz, Chem. Eur. J. 2012, 18, 40-49
31. N. Dietl, M. Schlangen, H. Schwarz, Angew. Chem. 2012, 124, 5638-5650
32. Angew. Chem. Int. Ed. 2012, 51, 5544-5555.
33. P. B. Armentrout, J. L. Beauchamp, Acc. Chem. Res. 1989, 22, 315-321
34. J. C. Weisshaar, Acc. Chem. Res. 1993, 26, 213-219
35. P. B. Armentrout, Acc. Chem. Res. 1995, 28, 430-436
36. H. Schwarz, D. Schröder, Pure Appl. Chem. 2000, 72, 2319-2332.
37. T. J. Carlin, L. Sallans, C. J. Cassady, D. B. Jacobson, B. S. Freiser, J. Am. Chem. Soc. 1983, 105, 6320-6321.
38. Q. Zhang, M. T. Bowers, J. Phys. Chem. A 2004, 108, 9755-9761
39. M. Schlangen, H. Schwarz, Angew. Chem. 2007, 119, 5711-5715
40. Angew. Chem. Int. Ed. 2007, 46, 5614-5617.
41. M. Schlangen, H. Schwarz, Helv. Chim. Acta 2008, 91, 2203-2210.
42. D. Schröder, H. Schwarz, Angew. Chem. 1990, 102, 1468-1469
43. Angew. Chem. Int. Ed. Engl. 1990, 29, 1433-1434
44. M. F. Ryan, A. Fiedler, D. Schroeder, H. Schwarz, Organometallics 1994, 13, 4072-4081
45. Y.-M. Chen, D. E. Clemmer, P. B. Armentrout, J. Am. Chem. Soc. 1994, 116, 7815-7826
46. M. F. Ryan, A. Fiedler, D. Schröder, H. Schwarz, J. Am. Chem. Soc. 1995, 117, 2033-2040
47. D. Schröder, H. Schwarz, Angew. Chem. 1995, 107, 2126-2150
48. Angew. Chem. Int. Ed. Engl. 1995, 34, 1973-1995
49. D. Schröder, H. Schwarz, D. E. Clemmer, Y. Chen, P. B. Armentrout, V. I. Baranov, D. K. Böhme, Int. J. Mass. Spectrom. Ion Processes 1997, 161, 175-191
50. N. Dietl, C. vanderLinde, M. Schlangen, M. K. Beyer, H. Schwarz, Angew. Chem. 2011, 123, 5068-5072
51. Angew. Chem. Int. Ed. 2011, 50, 4966-4969.
52. A. Fiedler, I. Kretzschmar, D. Schroder, H. Schwarz, J. Am. Chem. Soc. 1996, 118, 9941-9952.
53. D. Schröder, H. Schwarz, Angew. Chem. 1991, 103, 987-989
54. Angew. Chem. Int. Ed. Engl. 1991, 30, 991-993.
55. M. Schlangen, D. Schröder, H. Schwarz, Angew. Chem. 2007, 119, 1667-1671
56. Angew. Chem. Int. Ed. 2007, 46, 1641-1644
57. O. Lakuntza, J. M. Matxain, F. Ruiperez, M. Besora, F. Maseras, J. M. Ugalde, M. Schlangen, H. Schwarz, Phys. Chem. Chem. Phys. 2012, 14, 9306-9310
58. - species:, Y. Dede, X. Zhang, M. Schlangen, H. Schwarz, M.-H. Baik, J. Am. Chem. Soc. 2009, 131, 12634-12642.
59. E. R. Fisher, J. L. Elkind, D. E. Clemmer, R. Georgiadis, S. K. Loh, N. Aristov, L. S. Sunderlin, P. B. Armentrout, J. Chem. Phys. 1990, 93, 2676-2691
60. D. E. Clemmer, J. L. Elkind, N. Aristov, P. B. Armentrout, J. Chem. Phys. 1991, 95, 3387-3393.
61. D. E. Clemmer, N. Aristov, P. B. Armentrout, J. Phys. Chem. 1993, 97, 544-552.
62. X. H. Zhang, H. Schwarz, Theor. Chem. Acc. 2011, 129, 389-399.
63. C. Elschenbroich, Organometallchemie, 5.ed., B.G. Teubner, Wiesbaden, 2005
64. Organotransition Metal Chemistry: From Bonding to Catalysis (Ed.:, J.F. Hartwig,), University Science Book, Sausalito, 2010.
65. R. Houriet, L. F. Halle, J. L. Beauchamp, Organometallics 1983, 2, 1818-1829
66. G. Czekay, T. Drewello, H. Schwarz, J. Am. Chem. Soc. 1989, 111, 4561-4563
67. G. Czekay, T. Drewello, K. Eller, W. Zummack, H. Schwarz, Organometallics 1989, 8, 2439-2446
68. A. Fiedler, D. Schröder, H. Schwarz, B. L. Tjelta, P. B. Armentrout, J. Am. Chem. Soc. 1996, 118, 5047-5055
69. D. Schröder, H. Schwarz, S. Polarz, M. Driess, Phys. Chem. Chem. Phys. 2005, 7, 1049-1053
70. P. Gruene, C. Trage, D. Schröder, H. Schwarz, Eur. J. Inorg. Chem. 2006, 4546-4552
71. M. Schlangen, H. Schwarz, ChemCatChem 2010, 2, 799-802.
72. C. J. Cassady, B. S. Freiser, J. Am. Chem. Soc. 1985, 107, 1566-1573.
73. S. Niu, M. B. Hall, Chem. Rev. 2000, 100, 353-406
74. A. J. Bell, A. Citra, J. M. Dyke, F. Ferrante, L. Gagliardi, P. Watts, Phys. Chem. Chem. Phys. 2004, 6, 1213-1218
75. D. Schröder, M. Engeser, H. Schwarz, E. C. E. Rosenthal, J. Döbler, J. Sauer, Inorg. Chem. 2006, 45, 6235-6245.
76. D. Schröder, S. Shaik, H. Schwarz, Acc. Chem. Res. 2000, 33, 139-145.
77. M. Blume, R. E. Watson, Proc. R. Soc. London Ser. A 1962, 270, 127-143
78. G. M. Cole, B. B. Garrett, Inorg. Chem. 1970, 9, 1898-1902
79. M. Vijayakumar, M. S. Gopinathan, J. Mol. Struct. THEOCHEM 1996, 361, 15-19.
80. Z. Cheng, K. Siu, R. Guevremont, S. Berman, J. Am. Soc. Mass Spectrom. 1992, 3, 281-288
81. D. Vukomanovic, J. A. Stone, Int. J. Mass Spectrom. 2000, 202, 251-259
82. M. K. Beyer, Mass Spectrom. Rev. 2007, 26, 517-541.
83. A. F. Holleman, E. Wiberg, Lehrbuch der Anorganischen Chemie, 101ed., Walter deGruyter, Berlin, 1995.
84. P. B. Armentrout, R. Georgiadis, Polyhedron 1988, 7, 1573-1581
85. Organometallic Ion Chemistry (Ed.:, B.S. Freiser,), Kluwer, Dordrecht, 1996.
86. 4 system as a reference:, D. Schröder, H. Schwarz, Can. J. Chem. 2005, 83, 1936-1940, and references cited therein.
87. Collision-rate calculations (, G. Gioumousis, D. P. Stevenson, J. Chem. Phys. 1958, 29, 294-299) were performed by using the following method
88. M. P. Langevin, Ann. Chim. Phys. 1905, 8, 245-288.
89. J. L. Elkind, P. B. Armentrout, Int. J. Mass. Spectrom. Ion Processes 1988, 83, 259-284
90. J. L. Elkind, P. B. Armentrout, J. Phys. Chem. 1985, 89, 5626-5636.
91. F. Weinhold, C. R. Landis, Discovering Chemistry with Natural Bond Orbitals, Wiley, Hoboken, 2012.
92. C. Trage, D. Schröder, H. Schwarz, Chem. Eur. J. 2005, 11, 619-627.
93. Scientific Instrument Services: Isotope Distribution Calculator and Mass Spec Plotter. http://www.sisweb.com/mstools/isotope.html.
94. D. Schröder, H. Schwarz, S. Schenk, E. Anders, Angew. Chem. 2003, 115, 5241-5244
95. Angew. Chem. Int. Ed. 2003, 42, 5087-5090
96. C. Trage, M. Diefenbach, D. Schröder, H. Schwarz, Chem. Eur. J. 2006, 12, 2454-2464.
97. Gaussian 09 (RevisionA.1), M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. Montgomery, J.A., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N.J. Millam, M. Klene, J.E. Knox, 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, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian Inc. Wallingford CT, 2009.
98. F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
99. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789
100. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
101. E. Miliordos, J. F. Harrison, K. L. C. Hunt, J. Chem. Phys. 2011, 135, 144111.
102. K. Fukui, J. Phys. Chem. 1970, 74, 4161-4163
103. K. Fukui, Acc. Chem. Res. 1981, 14, 363-368
104. C. Gonzalez, H. B. Schlegel, J. Phys. Chem. 1990, 94, 5523-5527
105. D. G. Truhlar, M. S. Gordon, Science 1990, 249, 491-498.