Coordination Networks of 3,3′-Dicyanodiphenylacetylene and Silver (I) Salts: Structural Diversity through Changes in Ligand Conformation and Counterion

Inorganic Chemistry

Volumn 36, Issue 14, 1997, Pages 2960-2968

  Hirsch, Keith A ^a   Wilson, Scott R ^a   Moore, Jeffrey S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001568341     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic970150j     Document Type: Article

References (38)

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2. (b) Fujita, M.; Kwon, Y. J.; Washizu, S.; Ogura, K. J. Am. Chem. Soc. 1994, 116, 1151.
3. (c) Gardner, G. B.; Venkataraman, D.; Moore, J. S.; Lee, S. Nature 1995, 374, 792.
4. (d) Venkataraman, D.; Gardner, G. B.; Lee, S.; Moore, J. S. J. Am. Chem. Soc. 1995, 117, 11600.
5. (e) Yaghi, O. M.; Li, G.; Li, H. Nature 1995, 378, 703.
6. (a) Hirsch, K. A., Venkataraman, D.; Wilson, S. R.; Moore, J. S.; Lee, S. J. Chem. Soc., Chem. Commun. 1995, 2199.
7. (b) Venkataraman, D.; Lee, S.; Moore, J. S.; Zhang, P.; Hirsch, K. A.; Gardner, G. B.; Covey, A. C.; Prentice, C. L. Chem. Mater. 1996, 8, 2030.
8. (c) Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765.
9. Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Acta Crystallogr. 1996, C52, 2419.
10. Spek, A. L. J. Appl. Crystallogr. 1988, 21, 578.
11. The SHELXTL X-ray structure inement package consists of SAINT Version 4, SHELXTL Version 5, and SMART Version 4 and is marketed by Siemens Industrial Automation, Inc., Madison, WI.
12. For earlier examples of palladium-catalyzed cross coupling reactions utilized to prepare phenylacetylenes, see: (a) Wu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 297. (b) Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. Xu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1354.
13. For earlier examples of palladium-catalyzed cross coupling reactions utilized to prepare phenylacetylenes, see: (a) Wu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 297. (b) Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. Xu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1354.
14. For earlier examples of palladium-catalyzed cross coupling reactions utilized to prepare phenylacetylenes, see: (a) Wu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 297. (b) Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. Xu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1354.
15. We have performed a comprehensive search of the Cambridge Structural Database in order to tabulate the coordination propensities of transition metals in their various oxidation states. This study indicates, quantitatively and with statistical reliability, that silver (I) most often adopts linear, trigonal planar, and tetrahedral coordination geometries. See: Venkataraman, D.; Du, Y.; Wilson, S. R.; Hirsch, K. A.; Zhang, P.; Moore, J. S. J. Chem. Educ., in press. The results of this study are also available on the Internet: http://sulfur.sc-s.uiuc.edu/.
16. For other examples of five- and six-coordinate silver (I), see: Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1895.
17. For other examples of coordination networks displaying Ag⋯Ag contacts, see: (a) Michaelides, A.; Kiritsas, V.; Skoulika, S.; Aubry, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1495. (b) Masciocchi, N.; Moret, M.; Cairati, P.; Sironi, A.; Ardizzoia, G. A.; La Monica, G. J. Am. Chem. Soc. 1994, 116, 7668. (c) Masciocchi, N.; Moret, M.; Cairati, P.; Sironi, A.; Ardizzoia, G. A.; La Monica, G. J. Chem. Soc., Dalton Trans. 1995, 1671. (d) Robinson, F.; Zaworotko, M. I. J. Chem. Soc., Chem. Commun. 1995, 2413. (e) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1996, 118, 295. It should be noted that 9b describes Ag⋯Ag contacts as long as 3.449(6) Å.
18. For other examples of coordination networks displaying Ag⋯Ag contacts, see: (a) Michaelides, A.; Kiritsas, V.; Skoulika, S.; Aubry, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1495. (b) Masciocchi, N.; Moret, M.; Cairati, P.; Sironi, A.; Ardizzoia, G. A.; La Monica, G. J. Am. Chem. Soc. 1994, 116, 7668. (c) Masciocchi, N.; Moret, M.; Cairati, P.; Sironi, A.; Ardizzoia, G. A.; La Monica, G. J. Chem. Soc., Dalton Trans. 1995, 1671. (d) Robinson, F.; Zaworotko, M. I. J. Chem. Soc., Chem. Commun. 1995, 2413. (e) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1996, 118, 295. It should be noted that 9b describes Ag⋯Ag contacts as long as 3.449(6) Å.
19. For other examples of coordination networks displaying Ag⋯Ag contacts, see: (a) Michaelides, A.; Kiritsas, V.; Skoulika, S.; Aubry, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1495. (b) Masciocchi, N.; Moret, M.; Cairati, P.; Sironi, A.; Ardizzoia, G. A.; La Monica, G. J. Am. Chem. Soc. 1994, 116, 7668. (c) Masciocchi, N.; Moret, M.; Cairati, P.; Sironi, A.; Ardizzoia, G. A.; La Monica, G. J. Chem. Soc., Dalton Trans. 1995, 1671. (d) Robinson, F.; Zaworotko, M. I. J. Chem. Soc., Chem. Commun. 1995, 2413. (e) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1996, 118, 295. It should be noted that 9b describes Ag⋯Ag contacts as long as 3.449(6) Å.
20. For other examples of coordination networks displaying Ag⋯Ag contacts, see: (a) Michaelides, A.; Kiritsas, V.; Skoulika, S.; Aubry, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1495. (b) Masciocchi, N.; Moret, M.; Cairati, P.; Sironi, A.; Ardizzoia, G. A.; La Monica, G. J. Am. Chem. Soc. 1994, 116, 7668. (c) Masciocchi, N.; Moret, M.; Cairati, P.; Sironi, A.; Ardizzoia, G. A.; La Monica, G. J. Chem. Soc., Dalton Trans. 1995, 1671. (d) Robinson, F.; Zaworotko, M. I. J. Chem. Soc., Chem. Commun. 1995, 2413. (e) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1996, 118, 295. It should be noted that 9b describes Ag⋯Ag contacts as long as 3.449(6) Å.
21. For other examples of coordination networks displaying Ag⋯Ag contacts, see: (a) Michaelides, A.; Kiritsas, V.; Skoulika, S.; Aubry, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1495. (b) Masciocchi, N.; Moret, M.; Cairati, P.; Sironi, A.; Ardizzoia, G. A.; La Monica, G. J. Am. Chem. Soc. 1994, 116, 7668. (c) Masciocchi, N.; Moret, M.; Cairati, P.; Sironi, A.; Ardizzoia, G. A.; La Monica, G. J. Chem. Soc., Dalton Trans. 1995, 1671. (d) Robinson, F.; Zaworotko, M. I. J. Chem. Soc., Chem. Commun. 1995, 2413. (e) Yaghi, O. M.; Li, H. J. Am. Chem. Soc. 1996, 118, 295. It should be noted that 9b describes Ag⋯Ag contacts as long as 3.449(6) Å.
22. Lawrance, G. A. Chem. Rev. 1986, 86, 17.
23. See. for example, 8 and the following: (a) MacGillivray, L. R.; Subrarnanian, S.; Zaworotko, M. J. J. Chem. Soc. Chem. Commun. 1994, 1325. (b) Munakata, M.; Wu, L. P.; Yamamoto. M.; Kuroda-Sowa, T.; Maekawa, M. J. Am. Chem. Soc. 1996, 118, 3117. (c) Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1990, 112, 1546. (d) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755. (e) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Am. Chem. Soc. 1995, 117, 4562. (f) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. Inorg. Chem. 1995, 34, 5698.
24. See. for example, 8 and the following: (a) MacGillivray, L. R.; Subrarnanian, S.; Zaworotko, M. J. J. Chem. Soc. Chem. Commun. 1994, 1325. (b) Munakata, M.; Wu, L. P.; Yamamoto. M.; Kuroda-Sowa, T.; Maekawa, M. J. Am. Chem. Soc. 1996, 118, 3117. (c) Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1990, 112, 1546. (d) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755. (e) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Am. Chem. Soc. 1995, 117, 4562. (f) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. Inorg. Chem. 1995, 34, 5698.
25. See. for example, 8 and the following: (a) MacGillivray, L. R.; Subrarnanian, S.; Zaworotko, M. J. J. Chem. Soc. Chem. Commun. 1994, 1325. (b) Munakata, M.; Wu, L. P.; Yamamoto. M.; Kuroda-Sowa, T.; Maekawa, M. J. Am. Chem. Soc. 1996, 118, 3117. (c) Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1990, 112, 1546. (d) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755. (e) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Am. Chem. Soc. 1995, 117, 4562. (f) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. Inorg. Chem. 1995, 34, 5698.
26. See. for example, 8 and the following: (a) MacGillivray, L. R.; Subrarnanian, S.; Zaworotko, M. J. J. Chem. Soc. Chem. Commun. 1994, 1325. (b) Munakata, M.; Wu, L. P.; Yamamoto. M.; Kuroda-Sowa, T.; Maekawa, M. J. Am. Chem. Soc. 1996, 118, 3117. (c) Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1990, 112, 1546. (d) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755. (e) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Am. Chem. Soc. 1995, 117, 4562. (f) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. Inorg. Chem. 1995, 34, 5698.
27. See. for example, 8 and the following: (a) MacGillivray, L. R.; Subrarnanian, S.; Zaworotko, M. J. J. Chem. Soc. Chem. Commun. 1994, 1325. (b) Munakata, M.; Wu, L. P.; Yamamoto. M.; Kuroda-Sowa, T.; Maekawa, M. J. Am. Chem. Soc. 1996, 118, 3117. (c) Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1990, 112, 1546. (d) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755. (e) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Am. Chem. Soc. 1995, 117, 4562. (f) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. Inorg. Chem. 1995, 34, 5698.
28. See. for example, 8 and the following: (a) MacGillivray, L. R.; Subrarnanian, S.; Zaworotko, M. J. J. Chem. Soc. Chem. Commun. 1994, 1325. (b) Munakata, M.; Wu, L. P.; Yamamoto. M.; Kuroda-Sowa, T.; Maekawa, M. J. Am. Chem. Soc. 1996, 118, 3117. (c) Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1990, 112, 1546. (d) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755. (e) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Am. Chem. Soc. 1995, 117, 4562. (f) Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. Inorg. Chem. 1995, 34, 5698.
29. 3, respectively. See: (a) Mingos, D. M. P.; Rohl, A. L. Inorg. Chem. 1991, 30, 3769. (b) Mingos, D. M. P.; Rohl, A. L. J. Chem. Soc., Dalton Trans. 1991, 3419.
30. 3, respectively. See: (a) Mingos, D. M. P.; Rohl, A. L. Inorg. Chem. 1991, 30, 3769. (b) Mingos, D. M. P.; Rohl, A. L. J. Chem. Soc., Dalton Trans. 1991, 3419.
31. 2c
32. Ermer and Lindenberg observed a small deformation in 4-fold interpenetrated diamondoid networks of the dipotassium and disodium salts of 1,2,5,7-adamantanetetracarboxylic acid. The deformation arises from the different packing requirements of the sodium and potassium ions which occupy channels in the two structures. It should be noted that this deformation is less substantial than those observed in the 9-fold diamondoid networks reported in 2c. For more on the 4-fold structures, see: Ermer, O.; Lindenberg, L. Chem. Ber. 1990, 123, 1111.
33. For other examples of interpenetrated diamondoid networks, see s 2, 9a, 11a-d, 14, and the following: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747. (b) Ermer, O. Aav. Mater. 1991, 3, 608. (c) Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696. (d) Wang, X.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1994, 116, 12119.
34. For other examples of interpenetrated diamondoid networks, see s 2, 9a, 11a-d, 14, and the following: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747. (b) Ermer, O. Aav. Mater. 1991, 3, 608. (c) Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696. (d) Wang, X.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1994, 116, 12119.
35. For other examples of interpenetrated diamondoid networks, see s 2, 9a, 11a-d, 14, and the following: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747. (b) Ermer, O. Aav. Mater. 1991, 3, 608. (c) Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696. (d) Wang, X.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1994, 116, 12119.
36. For other examples of interpenetrated diamondoid networks, see s 2, 9a, 11a-d, 14, and the following: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747. (b) Ermer, O. Aav. Mater. 1991, 3, 608. (c) Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696. (d) Wang, X.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1994, 116, 12119.
37. 3 by Mingos and Rohl. See 12.
38. 6- ions are significantly disordered. The notion of forming larger void spaces by increasing the size of framework components was suggested early by Powell. See: Powell, H. M. J. Chem. Soc. 1948, 61.