Structural Studies of Bis(cyclopentadienyl)molybdenum-Amino Acid Complexes

Zeitschrift fur Anorganische und Allgemeine Chemie

Volumn 629, Issue 14, 2003, Pages 2585-2590

  Vujevic, Goranka ^a   Janiak, Christoph ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Amino acids; Crystal structure, pi Stacking; Molybdenum; Molybdocene

Indexed keywords

AMINO ACID; BIS(CYCLOPENTADIENYL)MOLYBDENUM; LEUCINE; MOLYBDENUM COMPLEX; PHENYL GROUP; PHENYLALANINE; UNCLASSIFIED DRUG; VALINE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; PH; STRUCTURE ANALYSIS;

EID: 0347720912     PISSN: 00442313     EISSN: None     Source Type: Journal    
DOI: 10.1002/zaac.200300278     Document Type: Article

References (62)

1. H. Köpf, P. Köpf-Maier, Angew. Chem. Int. Ed. Engl. 1979, 18, 477. P. Köpf-Maier, H. Köpf, Z. Naturforsch. 1979, 34b, 805. P. Köpf-Maier, H. Köpf, Drugs Future 1986, 11, 297. P. Köpf-Maier, H. Köpf, Chem. Rev. 1987, 87, 1137. P. Köpf-Maier, H. Köpf in Metal Compounds in Cancer Chemotherapy (S. P. Fricker, Ed.), Chapman and Hall, London, 1994, p. 109. P. Köpf-Maier, H. Köpf, in Stand der präklinischen und klinischen Entwicklung eines neuen Cytostatikums (W. E. Berdel, J. Baumgart, F. Bach, Eds.), Zuckerschwert Verlag, München, 1995.
2. H. Köpf, P. Köpf-Maier, Angew. Chem. Int. Ed. Engl. 1979, 18, 477. P. Köpf-Maier, H. Köpf, Z. Naturforsch. 1979, 34b, 805. P. Köpf-Maier, H. Köpf, Drugs Future 1986, 11, 297. P. Köpf-Maier, H. Köpf, Chem. Rev. 1987, 87, 1137. P. Köpf-Maier, H. Köpf in Metal Compounds in Cancer Chemotherapy (S. P. Fricker, Ed.), Chapman and Hall, London, 1994, p. 109. P. Köpf-Maier, H. Köpf, in Stand der präklinischen und klinischen Entwicklung eines neuen Cytostatikums (W. E. Berdel, J. Baumgart, F. Bach, Eds.), Zuckerschwert Verlag, München, 1995.
3. H. Köpf, P. Köpf-Maier, Angew. Chem. Int. Ed. Engl. 1979, 18, 477. P. Köpf-Maier, H. Köpf, Z. Naturforsch. 1979, 34b, 805. P. Köpf-Maier, H. Köpf, Drugs Future 1986, 11, 297. P. Köpf-Maier, H. Köpf, Chem. Rev. 1987, 87, 1137. P. Köpf-Maier, H. Köpf in Metal Compounds in Cancer Chemotherapy (S. P. Fricker, Ed.), Chapman and Hall, London, 1994, p. 109. P. Köpf-Maier, H. Köpf, in Stand der präklinischen und klinischen Entwicklung eines neuen Cytostatikums (W. E. Berdel, J. Baumgart, F. Bach, Eds.), Zuckerschwert Verlag, München, 1995.
4. H. Köpf, P. Köpf-Maier, Angew. Chem. Int. Ed. Engl. 1979, 18, 477. P. Köpf-Maier, H. Köpf, Z. Naturforsch. 1979, 34b, 805. P. Köpf-Maier, H. Köpf, Drugs Future 1986, 11, 297. P. Köpf-Maier, H. Köpf, Chem. Rev. 1987, 87, 1137. P. Köpf-Maier, H. Köpf in Metal Compounds in Cancer Chemotherapy (S. P. Fricker, Ed.), Chapman and Hall, London, 1994, p. 109. P. Köpf-Maier, H. Köpf, in Stand der präklinischen und klinischen Entwicklung eines neuen Cytostatikums (W. E. Berdel, J. Baumgart, F. Bach, Eds.), Zuckerschwert Verlag, München, 1995.
5. H. Köpf, P. Köpf-Maier, Angew. Chem. Int. Ed. Engl. 1979, 18, 477. P. Köpf-Maier, H. Köpf, Z. Naturforsch. 1979, 34b, 805. P. Köpf-Maier, H. Köpf, Drugs Future 1986, 11, 297. P. Köpf-Maier, H. Köpf, Chem. Rev. 1987, 87, 1137. P. Köpf-Maier, H. Köpf in Metal Compounds in Cancer Chemotherapy (S. P. Fricker, Ed.), Chapman and Hall, London, 1994, p. 109. P. Köpf-Maier, H. Köpf, in Stand der präklinischen und klinischen Entwicklung eines neuen Cytostatikums (W. E. Berdel, J. Baumgart, F. Bach, Eds.), Zuckerschwert Verlag, München, 1995.
6. H. Köpf, P. Köpf-Maier, Angew. Chem. Int. Ed. Engl. 1979, 18, 477. P. Köpf-Maier, H. Köpf, Z. Naturforsch. 1979, 34b, 805. P. Köpf-Maier, H. Köpf, Drugs Future 1986, 11, 297. P. Köpf-Maier, H. Köpf, Chem. Rev. 1987, 87, 1137. P. Köpf-Maier, H. Köpf in Metal Compounds in Cancer Chemotherapy (S. P. Fricker, Ed.), Chapman and Hall, London, 1994, p. 109. P. Köpf-Maier, H. Köpf, in Stand der präklinischen und klinischen Entwicklung eines neuen Cytostatikums (W. E. Berdel, J. Baumgart, F. Bach, Eds.), Zuckerschwert Verlag, München, 1995.
7. Titanium complexes in cancer treatment: E. Mendelez, Crit. Rev. Oncol. Hematol. 2002, 42, 309.
8. Antitumor metallocenes: M. M. Harding, G. Mokdsi, Curr. Med. Chem. 2000, 7, 1289.
9. 2: P. Köpf-Maier, H. Köpf, J. Organomet. Chem. 1988, 342, 167.
10. See also: P. Köpf-Maier, C. Janiak, H. Schumann, Inorg. Chim. Acta 1988, 152, 75. P. Köpf-Maier, C. Janiak, H. Schumann, J. Cancer Res. Clin. Oncology 1988, 114, 502.
11. See also: P. Köpf-Maier, C. Janiak, H. Schumann, Inorg. Chim. Acta 1988, 152, 75. P. Köpf-Maier, C. Janiak, H. Schumann, J. Cancer Res. Clin. Oncology 1988, 114, 502.
12. J. H. Toney, C. P. Brock, T. J. Marks, J. Am. Chem. Soc. 1985, 107, 947.
13. L. Kuo, L. A. Barnes, Inorg. Chem. 1999, 38, 814. L. Kuo, M. G. Kanatzidis, M. Sabat, A. L. Tripton, T. J. Marks, J. Am. Chem. Soc. 1991, 113, 9027.
14. L. Kuo, L. A. Barnes, Inorg. Chem. 1999, 38, 814. L. Kuo, M. G. Kanatzidis, M. Sabat, A. L. Tripton, T. J. Marks, J. Am. Chem. Soc. 1991, 113, 9027.
15. M. M. Harding, G. Mokdsi, J. P. Mackay, M. Prodigalidad, S. W. Lucas, Inorg. Chem. 1998, 37, 2432.
16. I. C. Tornieporth-Oetting, P S. White, Organometallics 1995, 14, 1632.
17. T. M. Klapötke, H. Köpf, I. C. Tornieporth-Oetting, P. S. White, Organometallics 1994, 13, 3628.
18. D. Harmsen, G. Erker, R. Fröhlich, G. Kehr, Eur. J. Inorg. Chem. 2002, 3156. J. Wonnemann, M. Oberhoff, G. Erker, R. Fröhlich, K. Bergander, Eur. J. Inorg. Chem. 1999, 1111.
19. D. Harmsen, G. Erker, R. Fröhlich, G. Kehr, Eur. J. Inorg. Chem. 2002, 3156. J. Wonnemann, M. Oberhoff, G. Erker, R. Fröhlich, K. Bergander, Eur. J. Inorg. Chem. 1999, 1111.
20. E. S. Gore, M. L. H. Green, J. Chem. Soc. A 1970, 2315.
21. K. Prout, S. R. Critchley, E. Cannillo, V. Tazzoli, Acta Crystallogr. 1977, B33, 456.
22. CSD version 5.24 (November 2002) with updates February 2003, April 2003 and July 2003.
23. W. Beck, K. Severin, Chem. Unserer Zeit 2002, 36, 356. K. Severin, R. Bergs, W. Beck, Angew. Chem. Int. Ed. 1998, 37, 1634.
24. W. Beck, K. Severin, Chem. Unserer Zeit 2002, 36, 356. K. Severin, R. Bergs, W. Beck, Angew. Chem. Int. Ed. 1998, 37, 1634.
25. Recent examples: W. Ponikwar, W. Beck, Z. Naturforsch. 2003, 58b, 318. M. A. Lang, K. Sünkel, W. Ponikwar, W. Beck, Z. Naturforsch. 2003, 58b, 311. K. Haas, W. Beck, Z. Anorg. Allg. Chem. 2002, 628, 788.
26. Recent examples: W. Ponikwar, W. Beck, Z. Naturforsch. 2003, 58b, 318. M. A. Lang, K. Sünkel, W. Ponikwar, W. Beck, Z. Naturforsch. 2003, 58b, 311. K. Haas, W. Beck, Z. Anorg. Allg. Chem. 2002, 628, 788.
27. Recent examples: W. Ponikwar, W. Beck, Z. Naturforsch. 2003, 58b, 318. M. A. Lang, K. Sünkel, W. Ponikwar, W. Beck, Z. Naturforsch. 2003, 58b, 311. K. Haas, W. Beck, Z. Anorg. Allg. Chem. 2002, 628, 788.
28. Recent examples: T. P. Curran, A. L. Grant, R. A. Lucht, J. C. Carter, J. Affonso, Organic Letters 2002, 4, 2917. D. R. van Staveren, E. Bothe, T. Weyhermüller, N. Metzler-Nolte, Eur. J. Inorg. Chem. 2002, 1518.
29. Recent examples: T. P. Curran, A. L. Grant, R. A. Lucht, J. C. Carter, J. Affonso, Organic Letters 2002, 4, 2917. D. R. van Staveren, E. Bothe, T. Weyhermüller, N. Metzler-Nolte, Eur. J. Inorg. Chem. 2002, 1518.
30. W. Petri, J. Meder, M. Girnth-Weller, K. Bartel, V. Bejenke, G. Huttner, W. Beck, Chem. Ber. 1982, 115, 846.
31. M. Maurus, B. Aechter, W. Hoffmüller, K. Polborn, W. Beck, Z. Anorg. Allg. Chem. 1997, 623, 299.
32. M. L. H. Green, L. C. Mitchard, W. L. Silverthorn, J. Chem. Soc., Dalton Trans. 1973, 1402. H. Brunner, W. Nowak, D. K. Rastogi, Inorg. Chim. Acta 1979, 33, L115. H. Wanjek, U. Nagel, W. Beck, Chem. Ber. 1988, 121, 1021. E. Schuhmann, C. Robl, W. Beck, Z. Naturforsch. 1994, 49b, 1569.
33. M. L. H. Green, L. C. Mitchard, W. L. Silverthorn, J. Chem. Soc., Dalton Trans. 1973, 1402. H. Brunner, W. Nowak, D. K. Rastogi, Inorg. Chim. Acta 1979, 33, L115. H. Wanjek, U. Nagel, W. Beck, Chem. Ber. 1988, 121, 1021. E. Schuhmann, C. Robl, W. Beck, Z. Naturforsch. 1994, 49b, 1569.
34. M. L. H. Green, L. C. Mitchard, W. L. Silverthorn, J. Chem. Soc., Dalton Trans. 1973, 1402. H. Brunner, W. Nowak, D. K. Rastogi, Inorg. Chim. Acta 1979, 33, L115. H. Wanjek, U. Nagel, W. Beck, Chem. Ber. 1988, 121, 1021. E. Schuhmann, C. Robl, W. Beck, Z. Naturforsch. 1994, 49b, 1569.
35. M. L. H. Green, L. C. Mitchard, W. L. Silverthorn, J. Chem. Soc., Dalton Trans. 1973, 1402. H. Brunner, W. Nowak, D. K. Rastogi, Inorg. Chim. Acta 1979, 33, L115. H. Wanjek, U. Nagel, W. Beck, Chem. Ber. 1988, 121, 1021. E. Schuhmann, C. Robl, W. Beck, Z. Naturforsch. 1994, 49b, 1569.
36. C. Djordjevic, N. Vuletic, B. A. Jacobs, M. Lee-Renslo, E. Sinn, Inorg. Chem. 1997, 36, 1798.
37. C. Janiak, J. Chem. Soc., Dalton Trans. 2000, 3885.
38. π-Interactions between pyridyl-type ligands for comparison: E. Craven, C. Zhang, C. Janiak, G. Rheinwald, H. Lang, Z. Anorg. Allg. Chem. 2003, 629, in press. C. Zhang, C. Janiak, Z. Anorg. Allg. Chem. 2001, 627, 1972. C. Zhang, C. Janiak, J. Chem. Crystallogr. 2001, 31, 29; C. Janiak, S. Deblon, H.-P. Wu, M. J. Kolm, P. Klüfers, H. Piotrowski, P. Mayer, Eur. J. Inorg. Chem. 1999, 1507. H.-P. Wu, C. Janiak, G. Rheinwald, H. Lang, J. Chem. Soc., Dalton Trans. 1999, 183. C. Janiak, L. Uehlin, H.-P. Wu, P. Klüfers, H. Piotrowski, T. G. Scharmann, J. Chem. Soc., Dalton Trans. 1999, 3121. H.-P. Wu, C. Janiak, L. Uehlin, P. Klüfers, P. Mayer, Chem. Commun. 1998, 2637.
39. π-Interactions between pyridyl-type ligands for comparison: E. Craven, C. Zhang, C. Janiak, G. Rheinwald, H. Lang, Z. Anorg. Allg. Chem. 2003, 629, in press. C. Zhang, C. Janiak, Z. Anorg. Allg. Chem. 2001, 627, 1972. C. Zhang, C. Janiak, J. Chem. Crystallogr. 2001, 31, 29; C. Janiak, S. Deblon, H.-P. Wu, M. J. Kolm, P. Klüfers, H. Piotrowski, P. Mayer, Eur. J. Inorg. Chem. 1999, 1507. H.-P. Wu, C. Janiak, G. Rheinwald, H. Lang, J. Chem. Soc., Dalton Trans. 1999, 183. C. Janiak, L. Uehlin, H.-P. Wu, P. Klüfers, H. Piotrowski, T. G. Scharmann, J. Chem. Soc., Dalton Trans. 1999, 3121. H.-P. Wu, C. Janiak, L. Uehlin, P. Klüfers, P. Mayer, Chem. Commun. 1998, 2637.
40. π-Interactions between pyridyl-type ligands for comparison: E. Craven, C. Zhang, C. Janiak, G. Rheinwald, H. Lang, Z. Anorg. Allg. Chem. 2003, 629, in press. C. Zhang, C. Janiak, Z. Anorg. Allg. Chem. 2001, 627, 1972. C. Zhang, C. Janiak, J. Chem. Crystallogr. 2001, 31, 29; C. Janiak, S. Deblon, H.-P. Wu, M. J. Kolm, P. Klüfers, H. Piotrowski, P. Mayer, Eur. J. Inorg. Chem. 1999, 1507. H.-P. Wu, C. Janiak, G. Rheinwald, H. Lang, J. Chem. Soc., Dalton Trans. 1999, 183. C. Janiak, L. Uehlin, H.-P. Wu, P. Klüfers, H. Piotrowski, T. G. Scharmann, J. Chem. Soc., Dalton Trans. 1999, 3121. H.-P. Wu, C. Janiak, L. Uehlin, P. Klüfers, P. Mayer, Chem. Commun. 1998, 2637.
41. π-Interactions between pyridyl-type ligands for comparison: E. Craven, C. Zhang, C. Janiak, G. Rheinwald, H. Lang, Z. Anorg. Allg. Chem. 2003, 629, in press. C. Zhang, C. Janiak, Z. Anorg. Allg. Chem. 2001, 627, 1972. C. Zhang, C. Janiak, J. Chem. Crystallogr. 2001, 31, 29; C. Janiak, S. Deblon, H.-P. Wu, M. J. Kolm, P. Klüfers, H. Piotrowski, P. Mayer, Eur. J. Inorg. Chem. 1999, 1507. H.-P. Wu, C. Janiak, G. Rheinwald, H. Lang, J. Chem. Soc., Dalton Trans. 1999, 183. C. Janiak, L. Uehlin, H.-P. Wu, P. Klüfers, H. Piotrowski, T. G. Scharmann, J. Chem. Soc., Dalton Trans. 1999, 3121. H.-P. Wu, C. Janiak, L. Uehlin, P. Klüfers, P. Mayer, Chem. Commun. 1998, 2637.
42. π-Interactions between pyridyl-type ligands for comparison: E. Craven, C. Zhang, C. Janiak, G. Rheinwald, H. Lang, Z. Anorg. Allg. Chem. 2003, 629, in press. C. Zhang, C. Janiak, Z. Anorg. Allg. Chem. 2001, 627, 1972. C. Zhang, C. Janiak, J. Chem. Crystallogr. 2001, 31, 29; C. Janiak, S. Deblon, H.-P. Wu, M. J. Kolm, P. Klüfers, H. Piotrowski, P. Mayer, Eur. J. Inorg. Chem. 1999, 1507. H.-P. Wu, C. Janiak, G. Rheinwald, H. Lang, J. Chem. Soc., Dalton Trans. 1999, 183. C. Janiak, L. Uehlin, H.-P. Wu, P. Klüfers, H. Piotrowski, T. G. Scharmann, J. Chem. Soc., Dalton Trans. 1999, 3121. H.-P. Wu, C. Janiak, L. Uehlin, P. Klüfers, P. Mayer, Chem. Commun. 1998, 2637.
43. π-Interactions between pyridyl-type ligands for comparison: E. Craven, C. Zhang, C. Janiak, G. Rheinwald, H. Lang, Z. Anorg. Allg. Chem. 2003, 629, in press. C. Zhang, C. Janiak, Z. Anorg. Allg. Chem. 2001, 627, 1972. C. Zhang, C. Janiak, J. Chem. Crystallogr. 2001, 31, 29; C. Janiak, S. Deblon, H.-P. Wu, M. J. Kolm, P. Klüfers, H. Piotrowski, P. Mayer, Eur. J. Inorg. Chem. 1999, 1507. H.-P. Wu, C. Janiak, G. Rheinwald, H. Lang, J. Chem. Soc., Dalton Trans. 1999, 183. C. Janiak, L. Uehlin, H.-P. Wu, P. Klüfers, H. Piotrowski, T. G. Scharmann, J. Chem. Soc., Dalton Trans. 1999, 3121. H.-P. Wu, C. Janiak, L. Uehlin, P. Klüfers, P. Mayer, Chem. Commun. 1998, 2637.
44. π-Interactions between pyridyl-type ligands for comparison: E. Craven, C. Zhang, C. Janiak, G. Rheinwald, H. Lang, Z. Anorg. Allg. Chem. 2003, 629, in press. C. Zhang, C. Janiak, Z. Anorg. Allg. Chem. 2001, 627, 1972. C. Zhang, C. Janiak, J. Chem. Crystallogr. 2001, 31, 29; C. Janiak, S. Deblon, H.-P. Wu, M. J. Kolm, P. Klüfers, H. Piotrowski, P. Mayer, Eur. J. Inorg. Chem. 1999, 1507. H.-P. Wu, C. Janiak, G. Rheinwald, H. Lang, J. Chem. Soc., Dalton Trans. 1999, 183. C. Janiak, L. Uehlin, H.-P. Wu, P. Klüfers, H. Piotrowski, T. G. Scharmann, J. Chem. Soc., Dalton Trans. 1999, 3121. H.-P. Wu, C. Janiak, L. Uehlin, P. Klüfers, P. Mayer, Chem. Commun. 1998, 2637.
45. μ-Interactions between substituted phenyl groups for comparison: (a) C. Zhang, G. Rheinwald, V. Lozan, B. Wu, P.-G. Lassahn, H. Lang, C. Janiak, Z. Anorg. Allg. Chem., 2002, 628, 1259. (b) E. Craven, E. Mutlu, D. Lundberg, S. Temizdemir, S. Dechert, H. Brombacher, C. Janiak, Polyhedron 2002, 21, 553.
46. μ-Interactions between substituted phenyl groups for comparison: (a) C. Zhang, G. Rheinwald, V. Lozan, B. Wu, P.-G. Lassahn, H. Lang, C. Janiak, Z. Anorg. Allg. Chem., 2002, 628, 1259. (b) E. Craven, E. Mutlu, D. Lundberg, S. Temizdemir, S. Dechert, H. Brombacher, C. Janiak, Polyhedron 2002, 21, 553.
47. M. L. H. Green, J. A. McCleverty, L. Pratt, G. Wilkinson, J. Chem. Soc. 1961, 4854.
48. R. L. Cooper, M. L. H. Green, J. Chem. Soc. A 1967, 1155.
49. F. A. Cotton, G. Wilkinson, Z. Naturforsch. 1954, 9b, 417.
50. Gmelin Handbook on Organomolybdenum Compounds, Part 12, Berlin 1994, p. 61.
51. J. Elmsley, Die Elemente, W. de Gruyter, Berlin, 1994.
52. E. Craven, K. Abu-Shandi, C. Janiak, Z. Anorg. Allg. Chem. 2003, 629, 195.
53. SMART, Data Collection Program for the CCD Area-Detector System; SAINT, Data Reduction and Frame Integration Program for the CCD Area-Detector System. Bruker Analytical X-ray Systems, Madison, Wisconsin, USA, 1997.
54. G. Sheldrick, Program SADABS: Area-detector absorption correction, University of Göttingen, Germany, 1996.
55. G. M. Sheldrick, SHELXS-97, SHELXL-97, Programs for Crystal Structure Analysis, University of Göttingen, Germany, 1997.
56. M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Oak Ridge National Laboratory Report ORNL-6895, 1996; L. J. Farrugia, ORTEP 3 for Windows, Version 1.076, University of Glasgow, 1997-2002. L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
57. M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Oak Ridge National Laboratory Report ORNL-6895, 1996; L. J. Farrugia, ORTEP 3 for Windows, Version 1.076, University of Glasgow, 1997-2002. L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
58. M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Oak Ridge National Laboratory Report ORNL-6895, 1996; L. J. Farrugia, ORTEP 3 for Windows, Version 1.076, University of Glasgow, 1997-2002. L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
59. A. L. Spek, Acta Crystallogr. 1990, A46, C34. A. L. Spek, PLATON Version 29-11-98; L. J. Farrugia, Windows implementation, University of Glasgow, 1998.
60. A. L. Spek, Acta Crystallogr. 1990, A46, C34. A. L. Spek, PLATON Version 29-11-98; L. J. Farrugia, Windows implementation, University of Glasgow, 1998.
61. A. L. Spek, Acta Crystallogr. 1990, A46, C34. A. L. Spek, PLATON Version 29-11-98; L. J. Farrugia, Windows implementation, University of Glasgow, 1998.
62. H. D. Flack, Acta Crystallogr. 1983, A39, 876.