Gas-phase models for catalysis: Alkane activation and olefin epoxidation by the triatomic cation Ag2O+

Journal of the American Chemical Society

Volumn 129, Issue 49, 2007, Pages 15311-15318

  Roithová, Jana ^a,b   Schröder, Detlef ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ACTIVATION; ELECTROSPRAY IONIZATION; EPOXIDATION; OLEFINS; OXYGENATION; PARAFFINS; POSITIVE IONS; SILVER COMPOUNDS;

ATOM TRANSFER; NEUTRAL REAGENT; TRIATOMIC CATIONS;

CATALYST ACTIVITY;

ALKENE; CATION; ETHYLENE; PROPYLENE; SILVER NITRATE;

ALLYLIC REARRANGEMENT; ARTICLE; ATOM; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODEL; CHEMICAL REACTION; ELECTROSPRAY; EPOXIDATION; GAS; OXYGENATION; QUANTUM CHEMISTRY;

EID: 37049012491     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja075628p     Document Type: Article

References (85)

1. Stegelmann, C.; Schiødt, N. C.; Campbell, C. T.; Stoltze, P. J. Catal. 2004, 221, 630.
2. Nijhuis, T. A.: Makkee, M.; Moulijn, J. A.; Weckhuysen, B. M. Ind. Eng. Chem. Res. 2006, 45, 3447.
3. See also: (a) Barteau, M. A. Top. Catal. 2003, 22, 3.
4. (b) Barteau, M. A. Surf. Sci. 2006, 600, 5021.
5. For reviews about the gas-phase chemistry of metal oxides, see: (a) Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1973.
6. (b) Schröder, D.; Shaik, S.; Schwarz, H. Struct. Bonding (Berlin) 2000, 97, 91.
7. (c) Schröder, D.; Schwarz, H. Top. Organomet. Chem. 2007, 22, 1.
8. See also: (a) Linic, S.; Barteau, M. A. J. Am. Chem. Soc. 2002, 124, 310.
9. (b) Linic, S.; Barteau, M. A. J. Am. Chem. Soc. 2003, 125, 4034.
10. (c) Linic, S.; Piao, H.; Adib, K.; Barteau, M. A. Angew. Chem., Int. Ed. 2004, 43, 2918.
11. 2 appears rather unexpected (see text). In fact, the mass resolution in these previous measurements might have been too low for definitive conclusions. See: Socaciu, L. D.; Hagen, J.; Heiz, U.; Bernhardt, T. M.; Leisner, T.; Wöste, L. Chem. Phys. Lett. 2001, 340, 282.
12. Fenn, J. B.; Mann, M.; Meng, C. K.; Wong, S. F.; Whitehouse, C. M. Science 1989, 246, 64.
13. For a review also addressing the various conditions of electrospray ionization, see: Cech, N. B.; Enke, C. G. Mass Spectrom. Rev. 2001, 20, 362.
14. Schröder, D.; Weiske, T.; Schwarz, H. Int. J. Mass Spectrom. 2002, 219, 729.
15. (a) Schröder, D.; Schwarz, H.; Schenk, S.; Anders, E. Angew. Chem., Int. Ed. 2003, 42, 5087.
16. (b) Roithová, J.; Hrušák, J.; Schröder, D.; Schwarz, H. Inorg. Chim. Acta 2005, 358, 4287.
17. (c) Feyel, S.; Schröder, D.; Schwarz, H. J. Phys. Chem. A 2006, 110, 2647.
18. (d) Schröder, D.; Engeser, M.; Schwarz, H.; Rosenthal, E. C. E.; Döbler, J.; Sauer, J. Inorg. Chem. 2006, 45, 6235.
19. See also: Roithová, J.; Schröder, D. Phys. Chem. Chem. Phys. 2007, 9, 731.
20. Jagoda-Cwiklik, B.; Jungwirth, P.; Rulišek, L.; Milko, P.; Roithová, J.; Lemaire, J.; Maitre, P.; Ortega, J. M.; Schröder, D. ChemPhysChem 2007, 8, 1629.
21. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664.
22. Frisch, M. J.; et al. Gaussian 03, Revision C.02, Gaussian, Inc.: Wallingford CT, 2004.
23. Gilbert, R. G.; Smith, S. C. Theory of Unimolecular and Recombination Reactions; Blackwell Scientific Publications: Oxford, 1990; p 52.
24. Zhu, L.; Hase, W. L. Quantum Chemistry Program Exchange; Indiana University: Bloomington, 1994; Program No. QCPE 644.
25. Zhu, L.; Hase, W. L. Chem. Phys. Lett. 1990, 175, 117.
26. Nguyen, V. Q.; Sadílek, M.; Ferrier, J. G.; Frank, A. J.; Tureček, F. J. Phys. Chem. A. 1997, 101, 3789.
27. Koizumi, H.; Larson, M.; Muntean, F.; Armentrout, P. B. Int. J. Mass Spectrom. 2003, 228, 221.
28. Calculated using the Chemputer made by M. Winter, University of Sheffield; see: http://winter.group.shef.ac.uk/chemputer/.
29. In ESI, the ionization conditions can be varied systematically by adjusting the accelerating potentials in the medium-pressure section of the ESI source (ref 8). Often, increase of the so-called cone voltage leads to harder ionization conditions via multiple energizing conditions, but the details may differ for ESI sources from different manufacturers.
30. For previous examples of such reactions with various metals, see: (a) Cheng, Z. L.; Siu, K. W. M.; Guevremont, R.; Berman, S. S. Org. Mass Spectrom. 1992, 27, 1370.
31. (b) Schröder, D.; Holthausen, M. C.; Schwarz, H. J. Phys. Chem. B. 2004, 108, 14407.
32. (c) Schröder, D.; Roithová, J. Angew. Chem., Int. Ed. 2006, 45, 5705.
33. (d) Schröder, D.; Roithová, J.; Schwarz, H. Int. J. Mass Spectrom. 2006, 254, 197.
34. See also: Jackson, J. G.; Novichikhin, A.; Fonseca, R. W.; Holcombe, J. A. Spectrochim. Acta, Part B 1995, 50, 1423 and references therein.
35. + was performed in that work, see: Flurer, R. A.; Busch, K. L. J. Am. Chem. Soc. 1991, 113, 3656.
36. + clusters, loss of atomic oxygen was also observed as a favorable channel; however, the clusters were not mass selected, and expulsion of neutral AgO might thus have escaped detection (ref 26). Also in the accompanying theoretical study, loss of neutral AgO was not considered.
37. Schmidt, M.; Cahuzac, P.; Bréchignac, C.; Cheng, H.-P. J. Chem. Phys. 2003, 118, 10956.
38. (a) Selinger, A.; Schnabel, P.; Wiese, W.; Irion, M. P. Ber. Bunsen-Ges. Phys. Chem. 1990, 94, 1278.
39. (b) Synders, R.; Wautelet, M.; Gouttebaron, R.; Dauchot, J. P.; Hecq, M. Surf. Coat. Technol. 2003, 174, 1282.
40. Chen, Y.-M.: Armentrout, P. B. J. Chem. Phys. 1995, 103, 618.
41. (a) Bréchignac, C.; Cahuzac, P.; Leygnier, J.; Tigneres, I. Chem. Phys. Lett. 1999, 303, 304.
42. (b) Schmidt, M.; Masson, A.; Bréchignac, C. Phys. Rev. Lett. 2003, 91, 243401.
43. (c) Schmidt, M.; Masson, A.; Bréchignac, C. J. Chem. Phys. 2005, 122, 134712.
44. 2), see: Li, L.; Hackett, P. A.; Rayner, D. M. J. Chem. Phys. 1993, 99, 2583.
45. Ran, Q.; Schmude, R. W., Jr.; Gingerich, K. A.; Wilhite, D. W.; Kingcade, J. E., Jr. J. Phys. Chem. 1993, 97, 8535.
46. 3 can be considered to occur as continuously endothermic processes.
47. (a) Sharpe, P.; Cassady, C. J. Chem. Phys. Lett. 1992, 191, 111.
48. (b) Sharpe, P.; Campbell, J. M.; Cassady, C. J. Organometallics 1994, 13, 3077.
49. Manard, M. J.; Kemper, P. R.; Carpenter, C. J.; Bowers, M. T. Int. J. Mass Spectrom. 2005, 241, 99.
50. + as a product was observed even in the absence of any reaction partner and is attributed to hydrocarbon contaminants present in the background of the high-vacuum apparatus. All data given in the text and the tables are already corrected for this background reactivity.
51. Weisshaar, J. C. Acc. Chem. Res. 1993, 26, 213.
52. (a) Tjelta, B. L.; Armentrout, P. B. J. Am. Chem. Soc. 1996, 118, 9652.
53. (b) Cornehl, H. H.; Heinemann, C.; Schröder, D.; Schwarz, H. Organometallics 1995, 14, 992.
54. (a) Wesendrup, R.; Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1174.
55. (b) Schröder, D.; Schwarz, H.; Clemmer, D. E.; Chen, Y.-M.; Armentrout, P. B.; Baranov, V. I.; Böhme, D. K. Int. J. Mass Spectrom. Ion Processes 1997, 161, 177.
56. Thibblin, A. J. Phys. Org. Chem. 1998, 1, 161 and references therein.
57. (a) Loos, J.; Schröder, D.; Zummack, W.; Schwarz, H.; Thissen, R.; Dutuit, O. Int. J. Mass Spectrom. 2002, 214, 105.
58. (b) Trage, C.; Schröder, D.; Schwarz, H. Organometallics 2003, 22, 693 (addendum 2003, 22, 1348).
59. (c) Schlangen, M.; Schröder, D.; Schwarz, H. Helv. Chim. Acta 2005, 88, 1405.
60. (d) Butschke, B.; Schlangen, M.; Schröder, D.; Schwarz, H. Z. Naturforsch. B 2007, 62b, 309.
61. Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1433.
62. Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 991.
63. Kretzschmar, I.; Fiedler, A.; Harvey, J. N.; Schröder, D.; Schwarz, H. J. Phys. Chem. A 1997, 101, 6252.
64. Feyel, S.; Döbler, J.; Schröder, D.; Sauer, J.; Schwarz, H. Angew. Chem., Int. Ed. 2006, 45, 4681.
65. Saueressig, G.; Crowley, J. N.; Bergamaschi, P.; Bruhl, C.; Brenninkmeijer, C. A. M.; Fischer, H. J. Geophys. Res. Atmos. 2001, 106, 23127.
66. Engeser, M.; Schlangen, M.; Schröder, D.; Schwarz, H.; Yumura, T.; Yoshizawa, K. Organometallics 2003, 22, 3933.
67. (a) Schröder, D.; Fiedler, A.; Hrušák, J.; Schwarz, H. J. Am. Chem. Soc. 1992, 114, 1215.
68. (b) Shiota, Y.; Yoshizawa, K. J. Am. Chem. Soc. 2000, 122, 12317.
69. (c) Yoshizawa, K. Coord. Chem. Rev. 2002, 226, 251.
70. For an instructive discussion, see: Schreiner, P. Angew. Chem., Int. Ed. 2007, 46, 4217.
71. See also: Baer, T.; Mayer, P. M. J. Am. Soc. Mass Spectrom. 1997, 8, 103.
72. Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1431.
73. Carter, E. A.; Goddard, W. A, III. J. Catal. 1988, 112, 80.
74. (a) Linic, S.; Medlin, J. W.; Barteau, M. A. Langmuir 2002, 18, 5197.
75. (b) Enever, M.; Linic, S.; Uffalussy, K.; Vohs, J. M.; Barteau, M. A. J. Phys. Chem. B 2005, 109, 2227.
76. + isomers, see: Schwarz, J.; Wesendrup, R.; Schröder, D.; Schwarz, H. Chem. Ber. 1996, 129, 1463.
77. For an example of a rearrangement of a gaseous transition-metal complex induced by a single neutral molecule, see: Becker, H.; Schröder, D.; Zummack, W.; Schwarz, H. J. Am. Chem. Soc. 1994, 116, 1096.
78. In a neutral-loss (or -gain) scan, two mass analyzers are scanned simultaneously with a fixed mass difference (Δm) while the reaction of interest is allowed to occur in between them. For ethene as a neutral reagent and Δm = -16, only those ions are detected which can transfer an oxygen atom to the substrate. Also see: ref 10a.
79. (a) Willey, K. F.; Cheng, P. Y.; Bishop, M. B.; Duncan, M. A. J. Am. Chem. Soc. 1991, 113, 4721.
80. (b) Puskar, L.; Stace, A. J. J. Mol. Phys. 2005, 103, 1829.
81. Olson, R.; Varganov, S.; Gordon, M. S.; Metiu, H. Chem. Phys. Lett. 2005, 412, 416.
82. El Aribi, H.; Shoeib, T.; Ling, Y.; Rodriguez, C. F.; Hopkinson, A. C.; Siu, K. W. M. J. Phys. Chem. A 2002, 106, 2908 and references therein.
83. See also: Linic, S.; Barteau, M. A. J. Am. Chem. Soc. 2004, 126, 8086.
84. For gas-phase experiments with similar mixed bimetallic clusters, see: (a) Koszinowski, K.; Schröder, D.; Schwarz, H. J. Am. Chem. Soc. 2003, 125, 3676.
85. (b) Koszinowski, K.; Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. 2004, 43, 121.