Molecular Mechanics Modeling of the Cobaloximes and Reevaluation of the Parameters for Modeling of the Cobalt Corrins

Inorganic Chemistry

Volumn 37, Issue 10, 1998, Pages 2578-2581

  Marques, Helder M ^a   Warden, Collette ^a   Monye, Moses ^a   Shongwe, Musa S ^a   Brown, Kenneth L ^b  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

^b OHIO UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001413294     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic970800j     Document Type: Article

References (60)

1. (a) Comba, P. In Fundamental Principles of Molecular Modeling; Gans, W., Amann, A., Boeyens, J. C. A., Eds.; Plenum Press: New York, 1996; pp 167-187.
2. (b) Hay, B. P. Coord. Chem. Rev. 1993, 126, 177.
3. (c) Zimmer, M. Chem. Rev. 1995, 95, 2629.
4. Marques, H. M.; Brown, K. L. J. Mol. Struct. (THEOCHEM) 1995, 340, 97.
5. Munro, O. Q.; Bradley, J. C.; Hancock, R. D.; Marques, H. M.; Marsicano, F.; Wade, P. W. J. Am. Chem. Soc. 1992, 114, 7218.
6. (a) Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127.
7. (b) Allinger, N. L.; Yuh, Y. MM2(87); Distributed to academic users by the Quantum Chemistry Program Exchange (QCPE), University of Indiana, Bloomington, IN 47405, under special agreement with Molecular Design Ltd., San Leandro, CA.
8. Marques, H. M.; Brown, K. L. Inorg. Chem. 1995, 34, 3733.
9. Brown, K. L.; Marques, H. M. Polyhedron 1996, 15, 2187.
10. Marques, H. M.; Hicks, R. P.; Brown, K. L. J. Chem. Soc., Chem. Commun. 1996, 1427.
11. 2; bis(dimethylglyoximato); MeCbl, methylcobalamin; MM, molecular mechanics; MD, molecular dynamics; NpCbl, neopentylcobalamin; py, pyridine; rmsd, root-mean-square difference; SA, simulated annealing.
12. Bresciani-Pahor, N.; Forcolin, M.; Marzilli, L. G.; Randaccio, L.; Summers, M. F.; Toscano, P. J. Coord. Chem. Rev. 1985, 63, 1.
13. HYPEKCHEM, Version 4.5; Hypercube Ltd.: 1115 NW 4th Street, Gainesville, FL 32601.
14. Allinger, N. L.; Yuh, Y. H.; Lii, J. H. J. Am. Chem. Soc. 1989, 111, 8551.
15. (b) Lii, J. H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8566.
16. (c) Lii, J. H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8576.
17. (d) MM3 is available to academic users from QCPE and to all users from Tripos, Inc., 1699 South Hanley Road, St. Louis, MO 63144.
18. (a) Comba, P.; Hambley, T. W.; Okon, N. MOMEC, a molecular modeling package for inorganic compounds; Altenhoff & Schmitz: Dortmund, Germany, 1995.
19. (b) Comba, P. Inorg. Chem. 1989, 28, 426.
20. (a) Snow, M. R. J. Am. Chem. Soc. 1970, 92, 3610.
21. (b) Hambley, T. W.; Hawkins, C. J.; Palmer, J. A.; Snow, M. R. Austr. J. Chem. 1981, 34, 45.
22. (c) Bond, A. M.; Hambley, T. W.; Mann, D. R.; Snow, M. R. Inorg. Chem. 1987, 26, 2257.
23. Hay, B. P. Inorg. Chem. 1991, 30, 2876.
24. Ferguson, D. M.; Raber, D. J. J. Comput. Chem. 1990, 11, 1061.
25. For example: (a) Hancock, R. D.; McDougall, G. J. J. Am. Chem. Soc. 1980, 102, 6511. (b) Brubaker, G. R.; Johnson, D. W. Inorg. Chem. 1984, 23, 1591. (c) Vedani, A.; Dobler, M.; Dunitz, J. D. J. Comput. Chem. 1986, 7, 701. (d) Drew, M. G. B.; Nicholson, D. G. J. Chem. Soc., Dalton Trans. 1986, 1543. (e) Zimmer, M.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 1062. (f) Yoshikawa, Y. J. Comput. Chem. 1990, 11, 326. (g) O'Neill, F. M.; Boeyens, J. C. A. Inorg. Chem. 1995, 34, 1988.
26. For example: (a) Hancock, R. D.; McDougall, G. J. J. Am. Chem. Soc. 1980, 102, 6511. (b) Brubaker, G. R.; Johnson, D. W. Inorg. Chem. 1984, 23, 1591. (c) Vedani, A.; Dobler, M.; Dunitz, J. D. J. Comput. Chem. 1986, 7, 701. (d) Drew, M. G. B.; Nicholson, D. G. J. Chem. Soc., Dalton Trans. 1986, 1543. (e) Zimmer, M.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 1062. (f) Yoshikawa, Y. J. Comput. Chem. 1990, 11, 326. (g) O'Neill, F. M.; Boeyens, J. C. A. Inorg. Chem. 1995, 34, 1988.
27. For example: (a) Hancock, R. D.; McDougall, G. J. J. Am. Chem. Soc. 1980, 102, 6511. (b) Brubaker, G. R.; Johnson, D. W. Inorg. Chem. 1984, 23, 1591. (c) Vedani, A.; Dobler, M.; Dunitz, J. D. J. Comput. Chem. 1986, 7, 701. (d) Drew, M. G. B.; Nicholson, D. G. J. Chem. Soc., Dalton Trans. 1986, 1543. (e) Zimmer, M.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 1062. (f) Yoshikawa, Y. J. Comput. Chem. 1990, 11, 326. (g) O'Neill, F. M.; Boeyens, J. C. A. Inorg. Chem. 1995, 34, 1988.
28. For example: (a) Hancock, R. D.; McDougall, G. J. J. Am. Chem. Soc. 1980, 102, 6511. (b) Brubaker, G. R.; Johnson, D. W. Inorg. Chem. 1984, 23, 1591. (c) Vedani, A.; Dobler, M.; Dunitz, J. D. J. Comput. Chem. 1986, 7, 701. (d) Drew, M. G. B.; Nicholson, D. G. J. Chem. Soc., Dalton Trans. 1986, 1543. (e) Zimmer, M.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 1062. (f) Yoshikawa, Y. J. Comput. Chem. 1990, 11, 326. (g) O'Neill, F. M.; Boeyens, J. C. A. Inorg. Chem. 1995, 34, 1988.
29. For example: (a) Hancock, R. D.; McDougall, G. J. J. Am. Chem. Soc. 1980, 102, 6511. (b) Brubaker, G. R.; Johnson, D. W. Inorg. Chem. 1984, 23, 1591. (c) Vedani, A.; Dobler, M.; Dunitz, J. D. J. Comput. Chem. 1986, 7, 701. (d) Drew, M. G. B.; Nicholson, D. G. J. Chem. Soc., Dalton Trans. 1986, 1543. (e) Zimmer, M.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 1062. (f) Yoshikawa, Y. J. Comput. Chem. 1990, 11, 326. (g) O'Neill, F. M.; Boeyens, J. C. A. Inorg. Chem. 1995, 34, 1988.
30. For example: (a) Hancock, R. D.; McDougall, G. J. J. Am. Chem. Soc. 1980, 102, 6511. (b) Brubaker, G. R.; Johnson, D. W. Inorg. Chem. 1984, 23, 1591. (c) Vedani, A.; Dobler, M.; Dunitz, J. D. J. Comput. Chem. 1986, 7, 701. (d) Drew, M. G. B.; Nicholson, D. G. J. Chem. Soc., Dalton Trans. 1986, 1543. (e) Zimmer, M.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 1062. (f) Yoshikawa, Y. J. Comput. Chem. 1990, 11, 326. (g) O'Neill, F. M.; Boeyens, J. C. A. Inorg. Chem. 1995, 34, 1988.
31. For example: (a) Hancock, R. D.; McDougall, G. J. J. Am. Chem. Soc. 1980, 102, 6511. (b) Brubaker, G. R.; Johnson, D. W. Inorg. Chem. 1984, 23, 1591. (c) Vedani, A.; Dobler, M.; Dunitz, J. D. J. Comput. Chem. 1986, 7, 701. (d) Drew, M. G. B.; Nicholson, D. G. J. Chem. Soc., Dalton Trans. 1986, 1543. (e) Zimmer, M.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 1062. (f) Yoshikawa, Y. J. Comput. Chem. 1990, 11, 326. (g) O'Neill, F. M.; Boeyens, J. C. A. Inorg. Chem. 1995, 34, 1988.
32. (a) Munro, O. Q.; Marques, H. M.; Debrunner, P. G.; Mohanrao, K.; Scheidt, W. R. J. Am. Chem. Soc. 1995, 117, 935.
33. (b) Marques, H. M.; Munro, O. Q.; Grimmer, N. E.; Levendis, D. C.; Marsicano, F.; Pattrick, G.; Markoulides, T. J. Chem. Soc., Faraday Trans. 1995, 91, 1741.
34. Bresciani-Pahor, N.; Randaccio, L.; Toscano, P. J.; Sandercock, A. C.; Marzilli, L. G. J. Chem. Soc., Dalton Trans. 1982, 129.
35. Bresciani-Pahor, N.; Randaccio, L.; Toscano, P. J.; Marzilli, L. G. J. Chem. Soc., Dalton Trans. 1982, 567.
36. Randaccio, L.; Bresciani-Pahor, N.; Orbell, J. D.; Calligaris, M.; Summers, M. F.; Snyder, B.; Toscano, P. J.; Grossman, J.; Liotta, D. Organometallics 1985, 4, 469.
37. Bresciani-Pahor, N.; Orbell, J. D.; Randaccio, L. Croat. Chem. Acta 1984, 57, 433.
38. Randaccio, L.; Bresciani-Pahor, N.; Toscano, P. J.; Marzilli, L. G. J. Am. Chem. Soc. 1980, 102, 7372.
39. Bresciani-Pahor, N.; Calligaris, M.; Randaccio, L.; Marzilli, L. G. Inorg. Chim. Acta 1979, 32, 181.
40. Bigotto, A.; Zangrando, E.; Randaccio, L. J. Chem. Soc., Dalton Trans. 1976, 96.
41. Randaccio, L.; Bresciani-Pahor, N.; Toscano, P. J.; Marzilli, L. G. J. Am. Chem. Soc. 1981, 103, 6347.
42. Marzilli, L. G.; Toscano, P. J.; Randaccio, L.; Bresciani-Pahor, N.; Calligaris, M. J. Am. Chem. Soc. 1979, 101, 6754.
43. 21b
44. (b) Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 1994, 116, 909.
45. (a) Shelnutt, J. A.; Medforth, C. J.; Berber, M. D.; Barkigia, K. M.; Smith, K. M. J. Am. Chem. Soc. 1991, 113, 4077.
46. (b) Senge, M. O.; Medforth, C. J.; Sparks, L. D.; Shelnutt, J. A.; Smith, K. M. Inorg. Chem. 1993, 32, 1716.
47. 30c.
48. (a) Cornell, W. D.; Ciepalk, P.; Bayley, C. I.; Gould, I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179.
49. (b) Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Karplus, M. J. Comput. Chem. 1983, 4, 187.
50. (c) Pranate, J.; Wierschke, S.; Jorgensen, W. L. J. Am. Chem. Soc. 1991, 113, 2810.
51. Luo, L. B.; Chen, H. L.; Tang, W. X.; Zhang, Z. Y.; Mak, T. C. W. J. Chem. Soc., Dalton Trans. 1996, 4425.
52. Brown, K. L.; Satyanarayana, S. J. Am. Chem. Soc. 1992, 114, 5674.
53. Savage, H. F. J.; Lindley, P. F.; Finney, J. L.; Timmins, P. A. Acta Crystallogr. Sect. B, 1987, 43, 280.
54. Alcock, N. W.; Dixon, R. M.; Golding, B. T. J. Chem. Soc., Chem. Commun. 1985, 603.
55. 23 (b) Marzilli, L. G.; Epps, L. A.; Sorrell, T.; Kistenmacher, T. J. J. Am. Chem. Soc. 1975, 97, 3351.
56. The angle between the mean planes of N21, C4, C5, C6, N22, C9, and C10, and N24, C16, C15, C14, N23, C11, and C10, respectively.
57. (a) Kratky, C.; Färber, G.; Gruber, K.; Wilson, K.; Dauter, Z.; Nolting, H.-F.; Kronrat, R.; Kräutler, B. J. Am. Chem. Soc. 1995, 117, 4654.
58. (b) Rossi, M.; Glusker, J. P.; Randaccio, L.; Marzilli, L. G. J. Am. Chem. Soc. 1985, 107, 1729.
59. Pagano, T. G.; Marzilli, L. G.; Flocco, M. M.; Tsai, C.; Carrell, H. L.; Glusker, J. P. J. Am. Chem. Soc. 1991, 113, 531.
60. Brown, K. L.; Zou, X. Inorg. Chim. Acta, in press.