Radical-like activation of alkanes by the ligated copper oxide cation (phenanthroline)CuO+

Journal of Physical Chemistry B

Volumn 108, Issue 38, 2004, Pages 14407-14416

  Schröder, Detlef ^a   Holthausen, Max C ^b   Schwarz, Helmut ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; COPPER OXIDES; ELECTRON TUNNELING; IONIZATION; METHANOL; POSITIVE IONS; POTENTIAL ENERGY; PROBABILITY DENSITY FUNCTION; PROPYLENE;

CHEMOSELECTIVITY; COLLISION-INDUCED DISSOCIATION (CID); DENSITY FUNCTIONAL THEORY (DFT); ELECTROSPRAY IONIZATION (ESI);

PARAFFINS;

EID: 4944267510     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0496452     Document Type: Article

References (90)

1. (a) Fokin, A. A.; Schreiner, P. R. Chem. Rev. 2002, 102, 1551.
2. (b) Limberg, C. Angew. Chem. 2003, 115, 6112.
3. (c) Limberg, C. Angew. Chem., Int. Ed. Engl. 2003, 42, 5932.
4. (a) Schröder, D.; Schwarz, H. Angew. Chem. 1995, 107, 2126.
5. (b) Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1973.
6. (a) Schröder, D.; Schwarz, H.; Shaik, S. In Structure and Bonding; Meunier, B., Ed.; Springer: Berlin, 2000; Vol. 97, p 91.
7. (b) Schröder, D. In The Encyclopedia of Mass Spectrometry; Armentrout, P. B., Ed.; Elsevier: Amsterdam, 2003; Vol. 1, p 810.
8. (a) Feichtinger, D.; Plattner, D. A. J. Chem. Soc., Perkin Trans. 2 2000, 1023.
9. (b) Plattner, D. A.; Feichtinger, D.; El-Bahraoui, J.; Wiest, O. Int. J. Mass Spectrom. 2000, 196, 351.
10. (c) Feichtinger, D.; Plattner, D. A. Chem.-Eur. J. 2001, 7, 591.
11. (d) El-Bahraoui, J.; Wiest, O.; Feichtinger, D.; Plattner, D. A. Angew. Chem. 2001, 113, 2131.
12. (e) El-Bahraoui, J.; Wiest, O.; Feichtinger, D.; Plattner, D. A. Angew. Chem., Int. Ed. Engl. 2001, 40, 2073.
13. Schwarz, H.; Schröder, D. Pure Appl. Chem. 2000, 72, 2319.
14. (a) Brönstrup, M.; Schröder, D.; Kretzschmar, I.; Schwarz, H.; Harvey, J. N. J. Am. Chem. Soc. 2001, 123, 142.
15. (b) Trage, C.; Schröder, D.; Schwarz, H. Organometallics 2003, 22, 693 (addendum 2003, 22, 1348).
16. Schröder, D.; Eller, K.; Prüsse, T.; Schwarz, H. Organometallics 1991, 10, 2052.
17. Tjelta, B. L.; Armentrout, P. B. J. Am. Chem. Soc. 1995, 117, 5531.
18. (a) Kappes, M. M.; Staley, R. H. J. Am. Chem. Soc. 1981, 103, 1296.
19. (b) Kang, H.; Beauchamp, J. L. J. Am. Chem. Soc. 1986, 108, 5663.
20. (c) Buckner, S. W.; Gord, J. R.; Freiser, B. S. J. Am. Chem. Soc. 1988, 110, 6606.
21. (d) Schröder, D.; Schwarz, H. Angew. Chem. 1990, 102, 1466.
22. (e) Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1431.
23. (f) Schröder, D.; Schwarz, H. Helv. Chim. Acta 1992, 75, 1281.
24. (g) Ryan, M. F.; Stöckigt, D.; Schwarz, H. J. Am. Chem. Soc. 1994, 116, 9565.
25. (h) Caraiman, D.; Bohme, D. K. J. Phys. Chem. A 2002, 106, 9705.
26. (a) Stöckigt, D.; Schwarz, H. Chem. Ber. 1994, 127, 2499.
27. (b) Stöckigt, D.; Schwarz, H. Liebigs Ann. 1995, 429.
28. (c) Brönstrup, M.; Schröder, D.; Schwarz, H. Can. J. Chem. 1999, 77, 774.
29. Schröder, D.; Weiske, T.; Schwarz, H. Int. J. Mass Spectrom. 2002, 219, 729.
30. Because aqueous copper(II) solutions are corrosive, the stainless steel capillary of the commercial instrument was replaced by one made from fused silica.
31. Schröder, D.; Engeser, M.; Brönstrup, M.; Daniel, C.; Spandl, J.; Hartl, H. Int. J. Mass Spectrom. 2003, 225, 743
32. Calculated using the Sheffield Chemputer, see: http://www.shef.ac.uk/ chemistry/chemputer/index.html. (Copyright Mark Winter, University of Sheffield, U.K., 1993-2001).
33. Busch, K. L.; Glish, G. L.; McLuckey, S. A. Mass Spectrometry/ Mass Spectrometry: Techniques and Applications of Tandem Mass Spectrometry, VCH Publishers: Weinheim, 1988.
34. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
35. (b) Perdew, J. B. Phys. Rev. B 1986, 33, 8822.
36. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
37. (b) Stevens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
38. (a) Schäfer, A.; Hörn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571.
39. (b) Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829.
40. (a) Kendall, R. A.; Früchtl, H. A. Theor. Chem. Acc. 1997, 97, 158.
41. (b) Dunlap, B. I. THEOCHEM 2000, 529, 37.
42. Dunlap, B. I. J. Chem. Phys. 1983, 78, 3140.
43. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560.
44. (a) Douglas, M.; Kroll, N. M. Ann. Phys. 1974, 82, 89.
45. (b) Hess, B. A. Phys. Rev. A 1985, 32, 756.
46. (c) Hess, B. A. Phys. Rev. A 1986, 33, 3742.
47. (d) Jansen, G.; Hess, B. A. Phys. Rev. A 1989, 39, 6016.
48. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.3; Gaussian, Inc.: Pittsburgh, PA, 2003.
49. (a) Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218.
50. (b) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454.
51. (c) Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Phys. Chem. 1998, 108, 4439.
52. Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory, 2nd ed.; Wiley-VCH: Weinheim, 2001.
53. (a) Dunning, T. H., Jr. J. Chem. Phys 1989, 90, 1007.
54. (b) Dunning, T. H., Jr. J. Phys. Chem. A 2000, 104, 9062.
55. Howell, S. L.; Gordon, K. C. J. Phys. Chem. A 2004, 108, 2536.
56. Kohler, M.; Lreaty, J. A. Int. J. Mass Spectrom. Ion Processes 1997, 162, 17.
57. For other selected examples of metal-oxide ions formed upon ESI, see: (a) Dalgaard, P.; McKenzie, C. J. J. Mass Spectrom. 1999, 34, 1033. (b) Vachet, R. W:; Callahan, J. H. J. Mass Spectrom. 2000, 55, 311. Styles, M. L.; O'Hair, R. A. J.; McFayden, W. D.; Tannous, L.; Holmes, R. J.; Gable, R. W. J. Chem. Soc., Dalton Trans. 2000, 93. Li, F.; Byers, M. A.; Houk, R. S. J. Am. Soc. Mass Spectrom. 2003, 14, 671.
58. For other selected examples of metal-oxide ions formed upon ESI, see: (a) Dalgaard, P.; McKenzie, C. J. J. Mass Spectrom. 1999, 34, 1033. (b) Vachet, R. W:; Callahan, J. H. J. Mass Spectrom. 2000, 55, 311. Styles, M. L.; O'Hair, R. A. J.; McFayden, W. D.; Tannous, L.; Holmes, R. J.; Gable, R. W. J. Chem. Soc., Dalton Trans. 2000, 93. Li, F.; Byers, M. A.; Houk, R. S. J. Am. Soc. Mass Spectrom. 2003, 14, 671.
59. For other selected examples of metal-oxide ions formed upon ESI, see: (a) Dalgaard, P.; McKenzie, C. J. J. Mass Spectrom. 1999, 34, 1033. (b) Vachet, R. W:; Callahan, J. H. J. Mass Spectrom. 2000, 55, 311. Styles, M. L.; O'Hair, R. A. J.; McFayden, W. D.; Tannous, L.; Holmes, R. J.; Gable, R. W. J. Chem. Soc., Dalton Trans. 2000, 93. Li, F.; Byers, M. A.; Houk, R. S. J. Am. Soc. Mass Spectrom. 2003, 14, 671.
60. For other selected examples of metal-oxide ions formed upon ESI, see: (a) Dalgaard, P.; McKenzie, C. J. J. Mass Spectrom. 1999, 34, 1033. (b) Vachet, R. W:; Callahan, J. H. J. Mass Spectrom. 2000, 55, 311. Styles, M. L.; O'Hair, R. A. J.; McFayden, W. D.; Tannous, L.; Holmes, R. J.; Gable, R. W. J. Chem. Soc., Dalton Trans. 2000, 93. Li, F.; Byers, M. A.; Houk, R. S. J. Am. Soc. Mass Spectrom. 2003, 14, 671.
61. Eller, K. Schwarz, H. Chem. Rev. 1991, 91, 1121.
62. See also: Becker, H.; Schröder, D.; Zummack, W.; Schwarz, H. J. Am. Chem. Soc. 1994, 116, 1096.
63. (a) Brönstrup, M.; Schröder, D.; Schwarz, H. Chem.-Eur. J. 2000, 6, 91.
64. (b) Brönstrup, M.; Trage, C.; Schröder, D.; Schwarz, H. J. Am. Chem. Soc. 2000, 122, 699.
65. (a) Shaik, S.; Danovich, D.; Fiedler, A.; Schröder, D.; Schwarz, H. Helv. Chim. Acta 1995, 78, 1393.
66. (b) Schröder, D.; Shaik, S.; Schwarz, H. Acc. Chem. Res. 2000, 33, 139
67. Cooks, R. G.; Wong, P. S. H. Acc. Chem. Res. 1998, 31, 379.
68. Weaver, A.; Arnold, D. W.; Bradforfh, S. E.; Neumark, D. M. J. Chem. Phys. 1991, 94, 1740.
69. 2. Except for the difference of the apparent thresholds, no additional information or approximations are required.
70. Rodgers, M. T.; Walker, B.; Armentrout, P. B. Int. J. Mass Spectrom. 1999, 182/183, 99.
71. Jackson, T. C.; Jacobson, D. B.; Freiser, B. S. J. A. Chem. Soc. 1984, 106, 1252.
72. Loos, J.; Schröder, D.; Zummack, W.; Schwarz, H.; Thissen, R.; Dutuit, O. Int. J. Mass Spectrom. 2002, 214, 105.
73. + parent ion beam.
74. 7+ cation may also contribute to the bonding and without further conclusive characterization of the electronic situation, no predictions can be made as far as the bonding scheme is concerned. In any case, the reactivity described in this study can consistently be described with the radical-like mnemonic.
75. Only activation of the secondary C-H bond was considered computationally.
76. Groves, J. T. J. Chem. Educ. 1985, 62, 928.
77. For recent related findings in the context of dinuclear copper - oxygen species, see: (a) Spuhler, P.; Holthausen, M. C. Angew. Chem. 2003, 115, 6143. (b) Spuhler, P.; Holthausen, M. C. Angew. Chem., Int. Ed. 2003, 42, 5961.
78. For recent related findings in the context of dinuclear copper - oxygen species, see: (a) Spuhler, P.; Holthausen, M. C. Angew. Chem. 2003, 115, 6143. (b) Spuhler, P.; Holthausen, M. C. Angew. Chem., Int. Ed. 2003, 42, 5961.
79. Unless mentioned otherwise, all data are taken from the NIST Standard Reference Database Number 69, July 2001 Release, see: http:// webbook.nist.gov/chemistry/.
80. 7OH, whose exothermicity is underestimated by 0.33 eV at the TZVP-DKH level of theory (Table 1).
81. Nakao, H.; Hirao, K. J. Chem. Phys. 2001, 114, 7935.
82. Fiedler, A.; Schröder, D.; Shaik, S.; Schwarz, H. J. Am. Chem. Soc. 1994, 116, 10734.
83. Irigoas, A.; Elizade, O.; Silanes, I.; Fowler, J. E.; Ugalde, J. M. J. Am. Chem. Soc. 2000, 122, 114.
84. (a) Poli, R.; Harvey, J. N. Chem. Soc. Rev. 2003, 32, 1.
85. (b) Harvey, J. N.; Poli, R.; Smith, K. M. Coord. Chem. Rev. 2003, 238/239, 347.
86. Smith, M. B.; March, J. March's Advanced Organic Chemistry; Wiley-Interscience: New York, 2001; p 900 ff.
87. Schwarz, J.; Wesendrup, R.; Schröder, D.; Schwarz, D. Chem. Ber. 1996, 129, 1463.
88. Data taken from: Frenkel, M.; Marsh, K. N.; Wilhoit, R. C.; Kabo, G. J.; Roganov, G. N. Thermodynamics of Organic Compounds in the Gas State; Thermodynamics Research Center: College Station, TX, 1994; see http://srdat.nist.gov/cccbdb.
89. (a) Peterson, K. A.; Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys 1994, 100, 7410.
90. (b) Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys 1994, 101, 8877.