Activation of the sulfhydryl group by Mo centers: Kinetics of reaction of benzyl radical with a binuclear Mo(μ-SH)Mo complex and with arene and alkane thiols

Journal of the American Chemical Society

Volumn 126, Issue 21, 2004, Pages 6680-6691

  Franz, James A ^a   Birnbaum, Jerome C ^a   Kolwaite, Douglas S ^a   Linehan, John C ^a   Camaioni, Donald M ^a   Dupuis, Michel ^a  

^a PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BOND STRENGTH (CHEMICAL); CATALYSTS; ELECTRONIC STRUCTURE; FREE RADICALS; HYDROGEN BONDS; REACTION KINETICS;

HOMOGENEOUS CATALYST MODELS; HYDROGEN ATOM ABSTRACTIONS;

MOLYBDENUM COMPOUNDS;

2 MERCAPTONAPHTHALENE; ALKANE; FREE RADICAL; HYDROGEN; MOLYBDENUM; NAPHTHALENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL BINDING; COMPARATIVE STUDY; COMPLEX FORMATION; KINETICS; STRUCTURE ANALYSIS;

EID: 2542599145     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049321r     Document Type: Article

References (77)

1. (a) Whitehurst, Adv. Catal. 1998, 42, 345 and references therein.
2. (b) Transition Metal-Sulfur Chemistry; Stiefel, E. I., Matsumoto, K., Eds.; ACS Symposium Series 653; American Chemical Society: Washington, DC, 1996.
3. (c) Topsøe, H.; Clausen, B. S.; Massoth, F. E. In Catalysis, Science and Technology; Anderson, J. R., Boudart, M., Ed.; Hydrotreating Catalysis, Science and Technology, Vol. 11; Sprinter Verlag: Berlin, 1996.
4. Molybdenum Enzymes, Cofactors, and Model System; Stiefel, E. I., Coucouvanis, D., Newton, W. E., Eds.; ACS Symposium Series 535; American Chemical Society: Washington, DC, 1993.
5. Rauchfuss, T. B. Inorg. Chem. 2004, 43, 14-26.
6. Travert, A.; Nakamura, H.; van Santen, R. A.; Cristol, S.; Paul. J.-F.; Payen, E. J. Am. Chem. Soc. 2002, 124, 7084-7095.
7. 2. In Transition Metal-Sulfur Chemistry; Stiefel, E. I., Matsumoto, K., Eds.; ACS Symposium Series 653; American Chemical Society: Washington, DC, 1996; pp 154-175.
8. Rüchardt, C.; Gerst, M.; Ebenhoch, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1406.
9. Tang, L.; Papish, E. T.; Abramo, G. P.; Norton, J. R.; Baik, M.-H.; Friesner, R. A.; Rappe, A. J. Am. Chem. Soc. 2003, 125, 10093-10102 and references therein.
10. Rakowski DuBois, M.; VanDerveer, M. C.; DuBois, D. L.; Haltiwanger, R. C.; Miller, W. K. J. Am. Chem. Soc., 1980, 102, 7456.
11. DuBois, D. L.; Miller, W. K.; Rakowski DuBois, M. J. Am. Chem. Soc. 1981, 103, 3429.
12. (a) Franz, J. A.; Bushaw, B. A.; Alnajjar, M. S. J. Am. Chem. Soc. 1989, 111, 268.
13. (b) Alnajjar, M. S.; Garrossian, M. S.; Autrey, S. T.; Ferris, K. F.; Franz, J. A. J. Phys. Chem. 1992, 96, 7037.
14. Examples include: (a) Rakowski DuBois, M. Catalysis by Sulfido Bridged Dimolybdenum Complexes. In Catalysis by Di-and Polynuclear Metal Cluster Complexes; Adams, R. D., Cotton, F. A., Eds.; Wiley-VCH Inc.: New York, 1998; pp 127-143 and references therein.
15. (b) Reference 4.
16. (c) Sarker, N.; Bruno, J. W. J. Am. Chem. Soc. 1999, 121, 2174.
17. (d) Fettinger, J. C.; Kraatz, H. B.; Poli, R.; Quadrelli, E. A.; Torralba, R. C. Organometallics 1998, 17, 5767.
18. (d) Bayse, C. A.; Hall, M. B.; Pleune, B.; Poli, R. Organometallics 1998, 17, 4309.
19. (e) Hascall, T.; Murphy, V. J.; Parkin, G. Organometallics 1996, 15, 3910.
20. (f) Tsai, Y. C.; Johnson, M. J. A.; Mindiola, D. J.; Cummins, C. C. J. Am. Chem. Soc. 1999, 121, 10426.
21. (g) Nolan, S. P.; Lopez de la Vega, R.; Hoff, C. D. J. Organomet. Chem. 1986, 315, 187.
22. (h) Hoff, C. D. J. Organomet. Chem. 1985, 282, 201.
23. (i) Landrum, J. T.; Hoff, C. D. J. Organomet. Chem. 1985, 282, 215.
24. (a) Eisenberg, D. C.; Norton, J. R. Isr. J. Chem. 1991, 31, 55.
25. (b) Eisenberg, D. C.; Lawrie, C. J. C.; Moody, A. E.; Norton, J. R. J. Am. Chem. Soc. 1991, 113, 4888.
26. Franz, J. A.; Linehan, J. C.; Birnbaum, J. C.; Hicks, K. W.; Alnajjar, M. S. J. Am. Chem. Soc. 1999, 121, 9824.
27. (a) Tilset, M.; Parker, V. D. J. Am. Chem. Soc. 1989, 111, 6711.
28. (See also Additions and Corrections. J. Am. Chem. Soc. 1990, 112, 2843.)
29. (b) Reference 11g.
30. Franz, J. A.; Naushadali, S. K.; Alnajjar, M. S. J. Org. Chem., 1986, 51, 19.
31. (a) Macey, R. I.; Oster, G. F. Berkeley Madonna, version 8.0.1; 2000. See: http://www.berkeleymadonna.com/.
32. (b) Hinsberg, W.; Houle, F.; Allen, F.; Yoon, E. Chemical Kinetics Simulator, v. 101; IBM Almaden Research Center. See: https://www.almaden.ibm.com/st/computational_science/ck/ msim/.
33. (a) Birnbaum, J. C.; Godziela, G.; Maciejewski, M.; Tonker, T. L.; Haltiwanger, R. C.; Rakowski DuBois, M. Organometallics 1990, 9, 394.
34. (b) Birnbaum, J. C.; Laurie, J. C. V.; Rakowski DuBois, M. Organometallics 1990, 9, 156.
35. Brunner, H.; Meier, W.; Wachter, J.; Guggolz, E.; Zahn, T.; Ziegler, M. Organometallics 1982, 1, 1107-1113.
36. Beck, W.; Danzer, W.; Thiel, G. Angew. Chem., Int. Ed. Engl. 1973, 12, 582.
37. Rakowski DuBois, M.; Haltiwanger, R. C.; Miller, D. J.; Glatzmeier, G. J. Am. Chem. Soc. 1979, 101, 5245.
38. Casewit, C. J.; Coons, D. E.; Wright, L. L.; Miller, W. K.; DuBois, M. R. Organometallics 1986, 5, 951-955.
39. Rakowski DuBois, M.; DuBois, D. L.; VanDerVeer, M. C.; Haltiwanger, R. C. Inorg. Chem. 1981, 20, 3064.
40. Bruce, A. E.; Tyler, D. R. Inorg. Chem. 1984, 23, 3433-3434.
41. The authors thank the reviewers for pointing out the possible photolytic interconversion of 4 to 5.
42. Fischer, H. J. Am. Chem. Soc. 1986, 108, 3925.
43. Karatekin, E.; O'Shaughnessy, B.; Turro, N. J. J. Chem. Phys. 1998, 108, 9577.
44. Cramer, C. J. Essentials of Computational Chemistry, Theories and Models; John Wiley & Sons Ltd.: Chichester, West Sussex, U.K., 2003.
45. Henry, D. J.; Sullivan, M. B.; Radom, L. J. J. Chem. Phys. 2003, 118 (1) 4849-4860.
46. Evans, M. G.; Polanyi, M. Trans. Faraday Soc. 1938, 34, 11.
47. Colle, T. H.; Glaspie, P. S.; Lewis, E. S. J. Org. Chem. 1978, 43, 2722-2725.
48. (a) Nolan, S. P.; Lopez de la Vega, R.; Hoff, C. D. Organometallics 1986, 5, 2529.
49. (b) Reference 6a.
50. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
51. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
52. Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; Vol. 3, p 1.
53. (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
54. (b) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
55. (c) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
56. 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.11; Gaussian, Inc.: Pittsburgh, PA, 2001.
57. Straatsma, T. P.; Apra, E.; Windus, T. L.; Dupuis, M.; Bylaska, E. J.; de Jong, W.; Hirata, S.; Smith, D. M. A.; Hackler, M. T.; Pollack, L.; Harrison, R. J.; Nieplocha, J.; Tipparaju, V.; Krishnan, M.; Brown, E.; Cisneros, G.; Fann, G. I.; Fruchtl, H.; Garza, J.; Hirao, K.; Kendall, R.; Nichols, J. A.; Tsemekhman, K.; Valiev, M.; Wolinski, K.; Anchell, J.; Bernholdt, D.; Borowski, P.; Clark, T.; Clerc, D.; Dachsel, H.; Deegan, M.; Dyall, K.; Elwood, D.; Glendening, E.; Gutowski, M.; Hess, A.; Jaffe, J.; Johnson, B.; Ju, J.; Kobayashi, R.; Kutteh, R.; Lin, Z.; Littlefield, R.; Long, X.; Meng, B.; Nakajima, T.; Niu, S.; Rosing, M.; Sandrone, G.; Stave, M.; Taylor, H.; Thomas, G.; van Lenthe, J.; Wong, A.; Zhang, Z. NW Chem, A Computational Chemistry Package for Parallel Computers, version 4.5; Pacific Northwest National Laboratory: Richland, WA 99352-0999, U.S.A., High Performance Computational Chemistry Group, Pacific Northwest National Laboratory, Richland, WA 99352, U.S.A., 2003.
58. Check, C. E.; Faust, T. O.; Bailey, J. M.; Wright, B. J.; Gilbert, T. M. ; Sunderlin, L. S. J. Phys. Chem. A 2001, 105, 8111.
59. (a) Stevens, W.; Basch, H.; Krauss, J. Chem. Phys. 1984, 81, 6026.
60. (b) Stevens, W. J.; Krauss, M.; Basch, H.; Jasien, P. G. Can. J. Chem. 1992, 70, 612.
61. (c) Cundari, T. R.; Stevens, W. J. J. Chem. Phys. 1993, 98, 5555.
62. (a) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
63. (b) Blaudeau, J.-P.; McGrath, M. P.; Curtiss, L. A.; Radom, L. J. Chem. Phys. 1997, 107, 5016.
64. (c) Clark, T.; Chandrasekhar, J.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294.
65. McQuarrie, D. A. Statistical Mechanics; Harper and Row: New York, 1976.
66. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502.
67. DiLabio, G. A.; Pratt, D. A.; LoFaro, A. D.; Wright, J. S. J. Phys. Chem. A 1999, 103, 1653-1661.
68. (a) Reid, R. C.; Prausnitz, J. M.; Sherwood, T. K. The Properties of Liquids and Gases; McGraw-Hill: New York, 1977.
69. (b) Weast, R. C.; Astle, M. J. Handbook of Chemistry and Physics; CRC Press: Boca Raton, FL, 1982-83.
70. Fischer, H.; Paul, H. Acc. Chem. Res. 1987, 20, 200.
71. (a) Lehni, M.; Schuh, H.; Fischer, H. Int. J. Chem. Kinet. 1979, 11, 705.
72. (b) Claridge, R. F. C.; Fischer, H. J. Phys. Chem. 1983, 87, 1960.
73. (c) Huggenberger, C.; Fischer, H. Helv. Chim. Acta 1981, 64, 338.
74. Franz, J. A.; Suleman, N. K.; Alnajjar, M. S. J. Org. Chem. 1986, 51, 19.
75. -1) = 27.23-2952.47/RT. A similar treatment for benzyl self-termination in toluene is in near-perfect agreement with experimental values (ref 42).
76. -1) = 27.23-2952.47/RT. A similar treatment for benzyl self-termination in toluene is in near-perfect agreement with experimental values (ref 42).
77. -1) = 27.23-2952.47/RT. A similar treatment for benzyl self-termination in toluene is in near-perfect agreement with experimental values (ref 42).