Consanguineous families of coordinated carbon: A ReC4Re assembly that is isolable in three oxidation states, including crystallographically characterized ReC ≡ CC ≡ CRe and +Re = C = C = C = C = Re+ adducts and a radical cation in which charge is delocalized between rhenium termini

Journal of the American Chemical Society

Volumn 119, Issue 4, 1997, Pages 775-788

  Brady, Monika ^a   Weng, Weiqing ^a   Zhou, Yuanlin ^a   Seyler, Jeffery W ^a   Amoroso, Angelo J ^a   Arif, Atta M ^a   Böhme, Marlis ^b   Frenking, Gernot ^b   Gladysz, J A ^a  

^a UNIVERSITY OF UTAH   (United States)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

RHENIUM COMPLEX;

ARTICLE; COMPLEX FORMATION; CRYSTALLOGRAPHY; ELECTROCHEMISTRY; REACTION ANALYSIS;

EID: 0031053918     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9631817     Document Type: Article

References (117)

1. University of Utah.
2. Philipps-Universität Marburg.
3. Ward, M. D. Chem. Soc. Rev. 1995, 121.
4. Astruc, D. Electron Transfer and Radical Processes in Transition Metal Chemistry; VCH: New York, 1995; Part I.
5. Some recent lead papers: (a) Lin, V. S.-Y.; DiMagno, S. G.; Therien, M. J. Science 1994, 264, 1105. (b) Sauvage, J.-P.; Collin, J.-P.; Chambron, J.-C.; Guillerez, S.; Coudret, C.; Balzani, V.; Barigelletti, F.; De Cola, L.; Flamigni, L. Chem. Rev. 1994, 94, 993.
6. Some recent lead papers: (a) Lin, V. S.-Y.; DiMagno, S. G.; Therien, M. J. Science 1994, 264, 1105. (b) Sauvage, J.-P.; Collin, J.-P.; Chambron, J.-C.; Guillerez, S.; Coudret, C.; Balzani, V.; Barigelletti, F.; De Cola, L.; Flamigni, L. Chem. Rev. 1994, 94, 993.
7. Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 21.
8. (a) Creutz, C. Prog. Inorg. Chem. 1983, 30, 1.
9. (b) Crutchley, R. J. Adv. Inorg. Chem. 1994, 41, 273.
10. See the following reviews, and references cited therein: (a) Ward, M. D. Chem. Ind. 1996, 568. (b) Harriman, A.; Ziessel, R. J. Chem. Soc., Chem. Commun. 1996, 1707.
11. See the following reviews, and references cited therein: (a) Ward, M. D. Chem. Ind. 1996, 568. (b) Harriman, A.; Ziessel, R. J. Chem. Soc., Chem. Commun. 1996, 1707.
12. Lagow, R. J.; Kampa, J. J.; Wei, H.-C.; Battle, S. L.; Genge, J. W.; Laude, D. A.; Harper, C. J.; Bau, R.; Stevens, R. C.; Haw, J. F.; Munson, E. Science 1995, 267, 362.
13. General reviews or perspectives: (a) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (b) Lang, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 547. (c) Bunz, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 969.
14. General reviews or perspectives: (a) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (b) Lang, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 547. (c) Bunz, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 969.
15. General reviews or perspectives: (a) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (b) Lang, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 547. (c) Bunz, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 969.
16. 2 complexes: Akita, M.; Moro-oka, Y. Bull. Chem. Soc. Jpn. 1995, 68, 420.
17. Preliminary communications of this work: (a) Zhou, Y.; Seyler, J. W.; Weng, W.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 8509. (b) Seyler, J. W.; Weng, W.; Zhou, Y.; Gladysz, J. A. Organometallics 1993, 12, 3802.
18. Preliminary communications of this work: (a) Zhou, Y.; Seyler, J. W.; Weng, W.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 8509. (b) Seyler, J. W.; Weng, W.; Zhou, Y.; Gladysz, J. A. Organometallics 1993, 12, 3802.
19. (a) Brady, M.; Weng, W.; Gladysz, J. A. J. Chem. Soc., Chem. Commun 1994, 2655.
20. (b) Bartik, T.; Bartik, B.; Brady, M.; Dembinski, R.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 414.
21. (c) Bartik, B.; Dembinski, R.; Bartik, T.; Arif, A. M.; Gladysz, J. A. New J. Chemistry 1997, in press.
22. Weng, W.; Bartik, T. ; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922.
23. (a) Weng, W.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1993, 115, 3824.
24. (b) Weng, W.; Bartik, T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1994, 33, 2199.
25. Weng, W.; Bartik. T.; Johnson, M. T.; Arif, A. M.; Gladysz, J. A. Organometallics 1995, 14, 889.
26. Ramsden, J. A.; Weng, W.; Gladysz, J. A. Organometallics 1992, 11, 3635.
27. Meyer, W. E.; Amoroso, A. J.; Gladysz, J. A., work in progress.
28. (a) Le Narvor, N.; Lapinte, C. J. Chem. Soc., Chem. Commun. 1993, 357.
29. (b) Le Narvor, N.; Toupet, L.; Lapinte, C. J. Am. Chem. Soc. 1995, 117, 7129.
30. (c) Coat, F.; Lapinte, C. Organometallics 1996, 15, 477.
31. n′ complexes: (a) Sonogashira, K.; Kataoka, S.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1978, 160, 319. (b) Wong, A.; Kang, P. C. W.; Tagge, C. D.; Leon, D. R. Organometallics 1990, 9, 1992. (c) Fyfe, H. B.; Mlekuz, M.; Zargarian, D.; Taylor, N. J.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1991, 188. (d) Stang, P. J.; Tykwinski, R. J. Am. Chem. Soc. 1992, 114, 4411. (e) Crescenzi, R.; Sterzo, C. L. Organometallics 1992, 11, 4301. (f) Rappert, T.; Nürnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (g) Bruce, M. I.; Hinterding, P.; Tiekink, E. R. T.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1993, 450, 209. (h) Yam, V. W.-W.; Lau, V. C.-Y.; Cheung, K.-K. Organometallics 1996, 15, 1740. (i) Gevert, O.; Wolf, J.; Werner, H. Organometallics 1996, 15, 2806. (j) Viola, E.; Lo Sterzo, C.; Trezzi, F. Organometallics 1996, 15, 4352.
32. n′ complexes: (a) Sonogashira, K.; Kataoka, S.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1978, 160, 319. (b) Wong, A.; Kang, P. C. W.; Tagge, C. D.; Leon, D. R. Organometallics 1990, 9, 1992. (c) Fyfe, H. B.; Mlekuz, M.; Zargarian, D.; Taylor, N. J.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1991, 188. (d) Stang, P. J.; Tykwinski, R. J. Am. Chem. Soc. 1992, 114, 4411. (e) Crescenzi, R.; Sterzo, C. L. Organometallics 1992, 11, 4301. (f) Rappert, T.; Nürnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (g) Bruce, M. I.; Hinterding, P.; Tiekink, E. R. T.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1993, 450, 209. (h) Yam, V. W.-W.; Lau, V. C.-Y.; Cheung, K.-K. Organometallics 1996, 15, 1740. (i) Gevert, O.; Wolf, J.; Werner, H. Organometallics 1996, 15, 2806. (j) Viola, E.; Lo Sterzo, C.; Trezzi, F. Organometallics 1996, 15, 4352.
33. n′ complexes: (a) Sonogashira, K.; Kataoka, S.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1978, 160, 319. (b) Wong, A.; Kang, P. C. W.; Tagge, C. D.; Leon, D. R. Organometallics 1990, 9, 1992. (c) Fyfe, H. B.; Mlekuz, M.; Zargarian, D.; Taylor, N. J.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1991, 188. (d) Stang, P. J.; Tykwinski, R. J. Am. Chem. Soc. 1992, 114, 4411. (e) Crescenzi, R.; Sterzo, C. L. Organometallics 1992, 11, 4301. (f) Rappert, T.; Nürnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (g) Bruce, M. I.; Hinterding, P.; Tiekink, E. R. T.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1993, 450, 209. (h) Yam, V. W.-W.; Lau, V. C.-Y.; Cheung, K.-K. Organometallics 1996, 15, 1740. (i) Gevert, O.; Wolf, J.; Werner, H. Organometallics 1996, 15, 2806. (j) Viola, E.; Lo Sterzo, C.; Trezzi, F. Organometallics 1996, 15, 4352.
34. n′ complexes: (a) Sonogashira, K.; Kataoka, S.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1978, 160, 319. (b) Wong, A.; Kang, P. C. W.; Tagge, C. D.; Leon, D. R. Organometallics 1990, 9, 1992. (c) Fyfe, H. B.; Mlekuz, M.; Zargarian, D.; Taylor, N. J.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1991, 188. (d) Stang, P. J.; Tykwinski, R. J. Am. Chem. Soc. 1992, 114, 4411. (e) Crescenzi, R.; Sterzo, C. L. Organometallics 1992, 11, 4301. (f) Rappert, T.; Nürnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (g) Bruce, M. I.; Hinterding, P.; Tiekink, E. R. T.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1993, 450, 209. (h) Yam, V. W.-W.; Lau, V. C.-Y.; Cheung, K.-K. Organometallics 1996, 15, 1740. (i) Gevert, O.; Wolf, J.; Werner, H. Organometallics 1996, 15, 2806. (j) Viola, E.; Lo Sterzo, C.; Trezzi, F. Organometallics 1996, 15, 4352.
35. n′ complexes: (a) Sonogashira, K.; Kataoka, S.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1978, 160, 319. (b) Wong, A.; Kang, P. C. W.; Tagge, C. D.; Leon, D. R. Organometallics 1990, 9, 1992. (c) Fyfe, H. B.; Mlekuz, M.; Zargarian, D.; Taylor, N. J.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1991, 188. (d) Stang, P. J.; Tykwinski, R. J. Am. Chem. Soc. 1992, 114, 4411. (e) Crescenzi, R.; Sterzo, C. L. Organometallics 1992, 11, 4301. (f) Rappert, T.; Nürnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (g) Bruce, M. I.; Hinterding, P.; Tiekink, E. R. T.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1993, 450, 209. (h) Yam, V. W.-W.; Lau, V. C.-Y.; Cheung, K.-K. Organometallics 1996, 15, 1740. (i) Gevert, O.; Wolf, J.; Werner, H. Organometallics 1996, 15, 2806. (j) Viola, E.; Lo Sterzo, C.; Trezzi, F. Organometallics 1996, 15, 4352.
36. n′ complexes: (a) Sonogashira, K.; Kataoka, S.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1978, 160, 319. (b) Wong, A.; Kang, P. C. W.; Tagge, C. D.; Leon, D. R. Organometallics 1990, 9, 1992. (c) Fyfe, H. B.; Mlekuz, M.; Zargarian, D.; Taylor, N. J.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1991, 188. (d) Stang, P. J.; Tykwinski, R. J. Am. Chem. Soc. 1992, 114, 4411. (e) Crescenzi, R.; Sterzo, C. L. Organometallics 1992, 11, 4301. (f) Rappert, T.; Nürnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (g) Bruce, M. I.; Hinterding, P.; Tiekink, E. R. T.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1993, 450, 209. (h) Yam, V. W.-W.; Lau, V. C.-Y.; Cheung, K.-K. Organometallics 1996, 15, 1740. (i) Gevert, O.; Wolf, J.; Werner, H. Organometallics 1996, 15, 2806. (j) Viola, E.; Lo Sterzo, C.; Trezzi, F. Organometallics 1996, 15, 4352.
37. n′ complexes: (a) Sonogashira, K.; Kataoka, S.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1978, 160, 319. (b) Wong, A.; Kang, P. C. W.; Tagge, C. D.; Leon, D. R. Organometallics 1990, 9, 1992. (c) Fyfe, H. B.; Mlekuz, M.; Zargarian, D.; Taylor, N. J.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1991, 188. (d) Stang, P. J.; Tykwinski, R. J. Am. Chem. Soc. 1992, 114, 4411. (e) Crescenzi, R.; Sterzo, C. L. Organometallics 1992, 11, 4301. (f) Rappert, T.; Nürnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (g) Bruce, M. I.; Hinterding, P.; Tiekink, E. R. T.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1993, 450, 209. (h) Yam, V. W.-W.; Lau, V. C.-Y.; Cheung, K.-K. Organometallics 1996, 15, 1740. (i) Gevert, O.; Wolf, J.; Werner, H. Organometallics 1996, 15, 2806. (j) Viola, E.; Lo Sterzo, C.; Trezzi, F. Organometallics 1996, 15, 4352.
38. n′ complexes: (a) Sonogashira, K.; Kataoka, S.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1978, 160, 319. (b) Wong, A.; Kang, P. C. W.; Tagge, C. D.; Leon, D. R. Organometallics 1990, 9, 1992. (c) Fyfe, H. B.; Mlekuz, M.; Zargarian, D.; Taylor, N. J.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1991, 188. (d) Stang, P. J.; Tykwinski, R. J. Am. Chem. Soc. 1992, 114, 4411. (e) Crescenzi, R.; Sterzo, C. L. Organometallics 1992, 11, 4301. (f) Rappert, T.; Nürnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (g) Bruce, M. I.; Hinterding, P.; Tiekink, E. R. T.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1993, 450, 209. (h) Yam, V. W.-W.; Lau, V. C.-Y.; Cheung, K.-K. Organometallics 1996, 15, 1740. (i) Gevert, O.; Wolf, J.; Werner, H. Organometallics 1996, 15, 2806. (j) Viola, E.; Lo Sterzo, C.; Trezzi, F. Organometallics 1996, 15, 4352.
39. n′ complexes: (a) Sonogashira, K.; Kataoka, S.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1978, 160, 319. (b) Wong, A.; Kang, P. C. W.; Tagge, C. D.; Leon, D. R. Organometallics 1990, 9, 1992. (c) Fyfe, H. B.; Mlekuz, M.; Zargarian, D.; Taylor, N. J.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1991, 188. (d) Stang, P. J.; Tykwinski, R. J. Am. Chem. Soc. 1992, 114, 4411. (e) Crescenzi, R.; Sterzo, C. L. Organometallics 1992, 11, 4301. (f) Rappert, T.; Nürnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (g) Bruce, M. I.; Hinterding, P.; Tiekink, E. R. T.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1993, 450, 209. (h) Yam, V. W.-W.; Lau, V. C.-Y.; Cheung, K.-K. Organometallics 1996, 15, 1740. (i) Gevert, O.; Wolf, J.; Werner, H. Organometallics 1996, 15, 2806. (j) Viola, E.; Lo Sterzo, C.; Trezzi, F. Organometallics 1996, 15, 4352.
40. n′ complexes: (a) Sonogashira, K.; Kataoka, S.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1978, 160, 319. (b) Wong, A.; Kang, P. C. W.; Tagge, C. D.; Leon, D. R. Organometallics 1990, 9, 1992. (c) Fyfe, H. B.; Mlekuz, M.; Zargarian, D.; Taylor, N. J.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1991, 188. (d) Stang, P. J.; Tykwinski, R. J. Am. Chem. Soc. 1992, 114, 4411. (e) Crescenzi, R.; Sterzo, C. L. Organometallics 1992, 11, 4301. (f) Rappert, T.; Nürnberg, O.; Werner, H. Organometallics 1993, 12, 1359. (g) Bruce, M. I.; Hinterding, P.; Tiekink, E. R. T.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1993, 450, 209. (h) Yam, V. W.-W.; Lau, V. C.-Y.; Cheung, K.-K. Organometallics 1996, 15, 1740. (i) Gevert, O.; Wolf, J.; Werner, H. Organometallics 1996, 15, 2806. (j) Viola, E.; Lo Sterzo, C.; Trezzi, F. Organometallics 1996, 15, 4352.
41. Lapinte, C.; Gladysz, J. A.; Paul, F.; Meyer, W. E., work in progress.
42. Eglinton, G.; McCrae, W. Adv. Org. Chem. 1963, 4, 225.
43. - are much smaller than in organic model compounds such as butadiyne and butatriene, presumably due to enhanced s character in the orbitals used for σ bonding to the electropositive rhenium. For related examples and further analysis, see: Caulton, K. G.; Cayton, R. H.; Chisholm, M. H.; Huffman, J. C.; Lobkovsky, E. B.; Xue, Z. Organometallics 1992, 11, 321 (Table V).
44. The SS,RR diastereomer and samples enriched in the SR,RS diastereomer gave identical data.
45. 13a,b,14 will be given in future full papers.
46. 2.
47. 19 and therefore closely comparable to those in (b).
48. (d) Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
49. 5 as > 19 kcal/mol (114°C): Patton, A. T.; Strouse, C. E.; Knobler, C. B.; Gladysz, J. A. J. Am. Chem. Soc. 1983, 105, 5804.
50. 0: (a) Senn, D. R.; Wong, A.; Patton, A. T.; Marsi, M.; Strouse, C. E.; Gladysz, J. A. J. Am. Chem. Soc. 1988, 110, 6096. (b) Kiel, W. A.; Lin, G.-Y.; Constable, A. G.; McCormick, F. B.; Strouse, C. E.; Eisenstein, O.; Gladysz, J. A. J. Am. Chem. Soc. 1982, 104, 4865. (c) Kowalczyk, J. J.; Arif, A. M.; Gladysz, J. A. Chem. Ber. 1991, 124, 729 and references therein.
51. 0: (a) Senn, D. R.; Wong, A.; Patton, A. T.; Marsi, M.; Strouse, C. E.; Gladysz, J. A. J. Am. Chem. Soc. 1988, 110, 6096. (b) Kiel, W. A.; Lin, G.-Y.; Constable, A. G.; McCormick, F. B.; Strouse, C. E.; Eisenstein, O.; Gladysz, J. A. J. Am. Chem. Soc. 1982, 104, 4865. (c) Kowalczyk, J. J.; Arif, A. M.; Gladysz, J. A. Chem. Ber. 1991, 124, 729 and references therein.
52. 0: (a) Senn, D. R.; Wong, A.; Patton, A. T.; Marsi, M.; Strouse, C. E.; Gladysz, J. A. J. Am. Chem. Soc. 1988, 110, 6096. (b) Kiel, W. A.; Lin, G.-Y.; Constable, A. G.; McCormick, F. B.; Strouse, C. E.; Eisenstein, O.; Gladysz, J. A. J. Am. Chem. Soc. 1982, 104, 4865. (c) Kowalczyk, J. J.; Arif, A. M.; Gladysz, J. A. Chem. Ber. 1991, 124, 729 and references therein.
53. 27
54. (a) Kriley, C. E.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1994, 116, 5225.
55. (b) Cotton, F. A.; Eglin, J. L.; Hong, B.; James, C. A. J. Am. Chem. Soc. 1992, 114, 4915.
56. (c) Hopkins, M. D.; Zietlow, T. C.; Miskowski, V. M.; Gray, H. B. J. Am. Chem. Soc. 1985, 107, 510.
57. Sandström, J. Dynamic NMR Spectroscopy; Academic Press: New York, 1982.
58. Tanimoto, M.; Kuchitsu, K.; Morino, Y. Bull. Chem. Soc. Jpn. 1971, 44, 386.
59. (a) Almenningen, A.; Bastiansen, O.; Trætteberg, M. Acta Chem. Scand. 1961, 15, 1557.
60. (b) Irngartinger, H.; Götzmann, W. Angew. Chem., Int. Ed. Engl. 1986, 25, 340.
61. (c) See, also: Morimoto, Y.; Higuchi, Y.; Wakamatsu, K.; Oshima, K.; Utimoto, K.; Yasuoka, N. Bull. Chem. Soc. Jpn. 1989, 62, 639.
62. - are within three esd values of each other, it can be questioned whether they are statistically different. However, note that the trend is reproduced in two independent determinations (footnote a, Table 3).
63. c values are furthermore solvent dependent, literature data should be compared with caution.
64. 1 values may depend slightly upon temperature.
65. 8 complex consisting of two vinylidene and two alkynyl linkages, and several configurational diastereomers.
66. Brunner, H.; Fisch, K.; Jones, P. G.; Salbeck, J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1521.
67. (a) Miller, J. S.; Dixon, D. A.; Calabrese, J. C.; Vazquez, C.; Krusic, P. J.; Ward, M. D.; Wasserman, E.; Harlow, R. L. J. Am. Chem. Soc. 1990, 112, 381.
68. -6 emu/mol).
69. 2 bridges: (a) Bruns, W.; Kaim, W.; Waldhör, E.; Krejčik, M. J. Chem. Soc., Chem. Commun. 1993, 1868 and Inorg. Chem. 1995, 34, 663. (b) Wlodarczyk, A.; Maher, J. P.; McCleverty, J. A.; Ward, M. D. J. Chem. Soc., Chem. Commun. 1995, 2397.
70. 2 bridges: (a) Bruns, W.; Kaim, W.; Waldhör, E.; Krejčik, M. J. Chem. Soc., Chem. Commun. 1993, 1868 and Inorg. Chem. 1995, 34, 663. (b) Wlodarczyk, A.; Maher, J. P.; McCleverty, J. A.; Ward, M. D. J. Chem. Soc., Chem. Commun. 1995, 2397.
71. 2 bridges: (a) Bruns, W.; Kaim, W.; Waldhör, E.; Krejčik, M. J. Chem. Soc., Chem. Commun. 1993, 1868 and Inorg. Chem. 1995, 34, 663. (b) Wlodarczyk, A.; Maher, J. P.; McCleverty, J. A.; Ward, M. D. J. Chem. Soc., Chem. Commun. 1995, 2397.
72. iso,Re values of 190 and 156 G: Walker, H. W.; Rattinger, G. B.; Belford, R. L.; Brown, T. L. Organometallics 1983, 2, 775.
73. -1).
74. (a) Frapper, G.; Kertesz, M. Inorg. Chem. 1993, 32, 732.
75. (b) Sponsler, M. B. Organometallics 1995, 14, 1920.
76. (c) Belanzoni, P.; Re, N.; Rosi M.; Sgamellotti, A.; Floriani, C. Organometallics 1996, 15, 4264
77. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
78. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: New York, 1990.
79. 2ρ(r) is the second derivative of the electron density ρ(r). A function is said to be concentrated in a region where its second derivative is negative. One way of comparing Figure 10a-c involves the tightly spaced solid contour lines that encircle C1-C4. These extend further from the atoms about π bonds (e.g., C1-C2 vs C2-C3 in Figure 10a).
80. -3.
81. Liang, C.; Allen, L. C. J. Am. Chem. Soc. 1991, 113, 1873.
82. Prior examples: (a) For ferrocene derivatives, see Schlögl, K.; Steyrer, W. J. Organomet. Chem. 1966, 6, 399. (b) Diederich, F.; Rubin, Y.; Chapman, O. L.; Goroff, N. S. Helv. Chim. Acta 1994, 77, 1441, and earlier references therein.
83. Prior examples: (a) For ferrocene derivatives, see Schlögl, K.; Steyrer, W. J. Organomet. Chem. 1966, 6, 399. (b) Diederich, F.; Rubin, Y.; Chapman, O. L.; Goroff, N. S. Helv. Chim. Acta 1994, 77, 1441, and earlier references therein.
84. Kim, P. J.; Masai, H.; Sonogashira, K.; Hagihara, N. Inorg. Nucl. Chem. Lett. 1970, 6, 181.
85. Takahashi, S.; Murata, E.; Sonogashira, K.; Hagihara, N. J. Poly. Sci. 1980, 18, 661.
86. x complexes I. For example, conjugal families would feature two unlike metal fragments. Many believe that there is a need for more humanistic metaphors, and fewer militaristic metaphors, in the chemical literature.
87. Peng, T.-S.; Winter, C. H.; Gladysz, J. A. Inorg. Chem. 1994, 33, 2534.
88. A sample of the cationic π ethyne complex that was a 95:5 enantiomer mixture has been converted to 2 that was a 71:29 diastereomer mixture: Bartik, B., unpublished results, 1994.
89. (a) Bally, T.; Roth, K.; Tang, W.; Schrock, R. R.; Knoll, K.; Park, L. Y. J. Am. Chem. Soc. 1992, 114, 2440.
90. (b) Atwood, C. G.; Geiger, W. E. J. Am. Chem. Soc. 1994, 116, 10849.
91. (a) Kober, E. M.; Goldsby, K. A.; Narayane, D. N. S.; Meyer, T. J. J. Am. Chem. Soc. 1983, 105, 4303, and references therein.
92. (b) Lay, P. A.; Magnuson, R. H.; Taube, H. Inorg. Chem. 1988, 27, 2364.
93. (c) Laidlaw, W. M.; Denning, R. G. J. Chem. Soc., Dalton Trans. 1995, 1987 and references therein.
94. For a caveat, see: Atwood, C. G.; Geiger, W. E.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 5310.
95. 34b Bardwell, D. A.; Horsburgh, L.; Jeffery, J. C.; Joulié, L. F.; Ward, M. D.; Webster, I.; Yellowlees, L. J. J. Chem. Soc., Dalton Trans. 1996, 2527.
96. 34b Bardwell, D. A.; Horsburgh, L.; Jeffery, J. C.; Joulié, L. F.; Ward, M. D.; Webster, I.; Yellowlees, L. J. J. Chem. Soc., Dalton Trans. 1996, 2527.
97. 34b Bardwell, D. A.; Horsburgh, L.; Jeffery, J. C.; Joulié, L. F.; Ward, M. D.; Webster, I.; Yellowlees, L. J. J. Chem. Soc., Dalton Trans. 1996, 2527.
98. 34b Bardwell, D. A.; Horsburgh, L.; Jeffery, J. C.; Joulié, L. F.; Ward, M. D.; Webster, I.; Yellowlees, L. J. J. Chem. Soc., Dalton Trans. 1996, 2527.
99. Binger, P.; Müller, P.; Phillips, P.; Gabor, B.; Mynott, R.; Herrmann, A. T.; Langhauser, F.; Krüger, C. Chem. Ber. 1992, 125, 2209.
100. (a) Worth, G. H.; Robinson, B. H.; Simpson, J. Organometallics 1992, 11, 3863.
101. (b) Osella, D.; Gambino, O.; Nevi, C.; Ravera, M.; Bertolino, D. Inorg. Chim. Acta 1993, 206, 155.
102. (a) Thomas, J. A.; Jones, C. J.; McCleverty, J. A.; Collison, D.; Mabbs, F. E.; Harding, C. J.; Hutchings, M. G. J. Chem. Soc., Chem. Commun. 1992, 1796.
103. (b) Tolbert, L. M.; Zhao, X.; Ding, Y.; Bottomley, L. A. J. Am. Chem. Soc. 1995, 117, 12891.
104. Zhou, Q.; Swager, T. M. J. Org. Chem. 1995, 60, 7096, and the introductory reference list therein.
105. m/z for most intense peak of isotope envelope; relative intensities are for the specified mass range.
106. CP 16 Hz, ReC).
107. Goodman, B. A.; Raynor, J. B. Adv. Inorg. Chem. Radiochem. 1970, 13, 135, 221.
108. (a) Frenz, B. A. in The Enraf-Nonius CAD 4 SDP - A Real-time System for Concurrent X-ray Data Collection and Crystal Structure Determination, In Computing and Crystallography; Schenk, H., Olthof-Hazelkamp, R., van Konigsveld, H., Bassi, G. C., Eds.; Delft University Press: Delft, Holland, 1978: pp 64-71.
109. (b) Sheldrick, G. M. SHELXS-93; University of Göttingen, 1993.
110. Sheldrick, G. M., manuscript in preparation for J. Appl. Cryst.
111. Cromer, D. T.; Waber, J. T. In International Tables for X-ray Crystallography; Ibers, J. A., Hamilton, W. C., Eds.; Kynoch: Birmingham, England 1974; Volume IV, Tables 2.2B and 2.3.1.
112. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
113. Bergner, A.; Dolg, M.; Küchle, W.; Stoll, H.; Preuss, H. Mol. Phys. 1993, 80, 1431.
114. Frenking, G.; Antes, I.; Böhme, M.; Dapprich, S.; Ehlers, A. W.; Jonas, V.; Neuhaus, A.; Otto, M.; Stegmann, R.; Veldkamp, A.; Vyboishchikov, S. F. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, Vol. 8, pp 63-144.
115. (a) Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Schlegel, H. B.; Raghavachari, K.; Robb, M. A.; Binkley, J. S.; Gonzalez, C.; Martin, R.; Fox, D. J.; DeFrees, D. J.; Baker, I.; Stewart, J. J. P.; Pople J. A., Gaussian Inc., Pittsburgh, PA 1992.
116. (b) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomberts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, I.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian Inc.: Pittsburgh, PA, 1995.
117. Biegler-König, F. W.; Bader, R. F. W.; Tang, T.-H. J. Comput. Chem. 1982, 3, 317.