Effects of the niobium(V) center on the energetics of ligand-centered proton and hydrogen atom transfer reactions in acyl and alkoxide complexes

Organometallics

Volumn 16, Issue 15, 1997, Pages 3249-3251

  Kerr, Margaret E ^a   Zhang, Xian Man ^a   Bruno, Joseph W ^a  

^a WESLEYAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041324411     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970224z     Document Type: Article

References (46)

1. (a) Costa, L. C. Catal. Rev.-Sci. Eng. 1983, 25, 325-363.
2. (b) Headford, C. E. L.; Roper, W. R. In Reactions of Coordinated Ligands; Braterman, P. S., Ed.; Plenum: New York, 1989.
3. (c) Choi, H. W.; Muetterties, E. L. Inorg. Chem. 1981, 20, 2664-2667.
4. (a) Loggenberg, P. M.; Carlton, L.; Copperthwaite, R. G.; Hutchings, G. J. J. Chem. Soc., Chem. Commun. 1987, 541-543.
5. (b) Jackson, J. E.; Bertsch, F. M. J. Am. Chem. Soc. 1990, 112, 9085-9092.
6. (c) Moloy, K. G.; Fagan, P. J.; Manriquez, J. M.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 56-67.
7. (d) Keim, W.; Roper, W. R.; Strutz, H. J. Organomet. Chem. 1981, 219, C5-C8.
8. (e) Brady, R. C.; Petit, R. J. Am. Chem. Soc. 1980, 102, 6182-6184.
9. (f) Biloven, P.; Helle, H. N.; Sachtler, W. M. H. J. Catal. 1979, 58, 95.
10. (g) Miller, R. L.; Toreki, R.; LaPointe, R. E.; Wolczanski, P. T.; Van Duyne, G. D.; Roe, D. C. J. Am. Chem. Soc. 1993, 115, 5570-5588.
11. (h) Chisholm, M. H.; Hammond, C. E.; Johnston, V. J.; Streib, W. E.; Huffman, J. C. J. Am. Chem. Soc. 1992, 114, 7056-7065.
12. Fermin, M. C.; Thiyagarajan, B.; Bruno, J. W. J. Am. Chem. Soc. 1993, 115, 974-979.
13. (a) Halfon, S. E.; Fermin, M. C.; Bruno, J. W. J. Am. Chem. Soc. 1989, 111, 5490-5491.
14. (b) Bruno, J. W.; Fermin, M. C.; Halfon, S. E.; Schulte, G. K. J. Am. Chem. Soc. 1989, 111, 8738-8740.
15. (c) Fermin, M. C.; Hneihen, A. S.; Maas, J. J.; Bruno, J. W. Organometallics 1993, 12, 1845-1856.
16. This difference has been shown to correspond to the difference in solvation of the proton in the two solvents: (a) Kolthoff, I. M.; Chantooni, M. K., Jr. J. Phys. Chem. 1972, 76, 2024-2034. (b) Krisjansdottir, S. S.; Norton, J. R. In Transition Metal Hydrides: Recent Advances in Theory and Experiment; Dedieu, A., Ed.; VCH: New York, 1992; Chapter 9.
17. This difference has been shown to correspond to the difference in solvation of the proton in the two solvents: (a) Kolthoff, I. M.; Chantooni, M. K., Jr. J. Phys. Chem. 1972, 76, 2024-2034. (b) Krisjansdottir, S. S.; Norton, J. R. In Transition Metal Hydrides: Recent Advances in Theory and Experiment; Dedieu, A., Ed.; VCH: New York, 1992; Chapter 9.
18. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463 and references therein.
19. (a) Bordwell, F. G.; Cheng, J.-P.; Harrelson, J. A., Jr. J. Am. Chem. Soc. 1988, 110, 1229-1234.
20. (b) Bordwell, F. G.; Cheng, J.-P.; Ji, G.-Z.; Satish, A. V.; Zhang, X.-M. J. Am. Chem. Soc. 1991, 113, 9790-9796.
21. (c) Bordwell, F. G.; Zhang, X.-M. Acc. Chem. Res. 1993, 26, 510-517.
22. (d) Arnett, E. M.; Amarnath, K.; Harvey, N. G.; Venimadhavan, S. J. Am. Chem. Soc. 1990, 112, 7346-7353.
23. (e) Arnett, E. M.; Amarnath, K.; Harvery, N. G.; Cheng, J. P. Science 1990, 247, 423-430.
24. (f) Tilset, M.; Parker, V. D. J. Am. Chem. Soc. 1989, 111, 6711-6718.
25. (g) Tilset, M. J. Am. Chem. Soc. 1992, 114, 2740-2741.
26. (h) Skagestad, V.; Tilset, M. J. Am. Chem. Soc. 1993, 115, 5077-5083.
27. (i) Smith, K.-T.; Romming, C.; Tilset, M. J. Am. Chem. Soc. 1993, 115, 8681-8689.
28. (j) Wang, D.; Angelici, R. J. J. Am. Chem. Soc. 1996, 118, 935-942.
29. (a) Parker, V. D.; Handoo, K. L.; Roness, F.; Tilset, M. J. Am. Chem. Soc. 1991, 113, 7493-7499.
30. (b) Wayner, D. D. M.; Parker, V. D. Acc. Chem. Res. 1993, 26, 287-293.
31. Hneihen, A. S.; Fermin, M. C.; Maas, J. J.; Bruno, J. W. J. Organomet. Chem. 1992, 429, C33-C37.
32. Zhang, X.-M.; Fry, A. J.; Bordwell, F. G. J. Org. Chem. 1996, 61, 4101-4106.
33. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications; Wiley: New York, 1980, Chapter 11. We thank a reviewer for helpful comments on the kinetic effects.
34. Bordwell, F. G.; Zhang, X.-M.; Filler, R. J. Org. Chem. 1993, 58, 6067-6071.
35. (a) Sutcliffe, R.; Griller, D.; Lessard, J.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 624-628.
36. (b) Danen, W. C.; Gellert, R. W. J. Am. Chem. Soc. 1980, 102, 3264-3265.
37. (a) Thiyagarajan, B.; Michalczyk, L.; Bollinger, J. C.; Huffman, J. C.; Bruno, J. W. Organometallics 1996, 15, 1989-1999.
38. (b) Thiyagarajan, B.; Kerr, M. E.; Bollinger, J. C.; Young, V. G., Jr.; Bruno, J. W. Organometallics 1997, 16, 1331-1334.
39. 15a was accounted for; the methodology has been described in refs 3 and 15b. (a) Isutzu, K. Acid-Base Dissoication Constants in Dipolar Aprotic Solvents; IUPAC Chemical Data Series 35; Blackwell Scientific: Oxford, U.K., 1990. (b) Moore, E. J.; Sullivan, J. M.; Norton, J. R. J. Am. Chem. Soc. 1986, 108, 2257-2263.
40. 15a was accounted for; the methodology has been described in refs 3 and 15b. (a) Isutzu, K. Acid-Base Dissoication Constants in Dipolar Aprotic Solvents; IUPAC Chemical Data Series 35; Blackwell Scientific: Oxford, U.K., 1990. (b) Moore, E. J.; Sullivan, J. M.; Norton, J. R. J. Am. Chem. Soc. 1986, 108, 2257-2263.
41. McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493-532.
42. 14b
43. (a) Diogo, H. P.; de Alencar Simoni, J.; Minas de Piedade, M. E.; Dias, A. R.; Martinho Simoes, J. A. J. Am. Chem. Soc. 1993, 115 2764-2774.
44. For a related study, see: (b) Lichtenberger, D. L.; Darsey, G. P.; Kellogg, G. E.; Sanner, R. D.; Young, V. G., Jr.; Clark, J. R. J. Am. Chem. Soc. 1989, 111, 5019-5028.
45. Connor, J. A. Top. Curr. Chem. 1977, 71, 71-110.
46. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row: New York, 1987; pp 164-170.