Molecular assembly of 1,3,5-tris(cyanomethyl) and 1,4-bis(cyanomethyl) arenes with silver triflate

Pure and Applied Chemistry

Volumn 78, Issue 4, 2006, Pages 855-871

  Kilway, Kathleen V ^a   Deng, Shiping ^a   Bowser, Sean ^a   Mudd, Joseph ^a   Washington, Laronda ^a   Ho, Douglas M ^b  

^a UNIVERSITY OF MISSOURI KANSAS CITY   (United States)

^b PRINCETON UNIVERSITY   (United States)

Author keywords

Molecular assembly; Network solids; Organonitriles; Silver salts; X ray diffraction

Indexed keywords

EID: 33645662426     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200678040855     Document Type: Conference Paper

References (60)

1. H. Weizman, J. Libman, A. Shanzer. J. Am. Chem. Soc. 120, 2188 (1998).
2. (a) D. D. MacNichol. In Inclusion Compounds 2, J. L. Atwood, J. E. D. Davies, D. D. MacNichol (Eds.), Chap. 5, Academic, New York (1984);
3. (b) F. Vögtle. Cyclophane Chemistry: Synthesis, Structures, and Reactions, John Wiley, Chichester (1993).
4. (a) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon. Acc. Chem. Res. 28, 37 (1995);
5. (b) N. Bowden, A. Terfort, J. Carbeck, G. M. Whitesides. Science 276, 233 (1997);
6. (c) A. Terfort, N. Bowden, G. M. Whitesides. Nature 386, 162 (1997).
7. (a) P. Tecilla, V. Jubian, A. D. Hamilton. Tetrahedron 51, 435 (1995);
8. (b) A. D. Hamilton. Adv. Supramol. Chem. 1, 1 (1991);
9. (c) S. C. Zimmerman. Top. Curr. Chem. 165, 71 (1993);
10. (d) C. M. Drain, R. Fischer, E. G. Nolen, J.-M. Lehn. J. Chem. Soc., Chem. Commun. 243 (1993);
11. (e) O. F. Schall, G. W. Gokel. J. Am. Chem. Soc. 116, 6089 (1994);
12. (f) V. A. Russell, M. C. Etter, M. D. Ward. J. Am. Chem. Soc. 116, 1941 (1994).
13. (a) A. W. Maverick, F. E. Klavetter. Inorg. Chem. 23, 4129 (1984);
14. (b) A. W. Maverick, S. C. Buckingham, Q. Yao, J. R. Bradbury, G. G. Stanley. J. Am. Chem. Soc. 108, 7430 (1986);
15. (c) J. R. Bradbury, J. L. Hampton, D. P. Marione, A. W. Maverick. Inorg. Chem. 28, 2392 (1989);
16. (d) A. W. Maverick, M. L. Ivie, J. H. Waggenspack, F. R. Fronczek. Inorg. Chem. 29, 2403 (1990).
17. K. A. Hirsch, D. Venkataraman, S. R. Wilson, J. S. Moore, S. Lee. J. Chem. Soc., Chem. Commun. 2199 (1995).
18. (a) P. J. Stang. Chem. Eur. J. 4, 19 (1998);
19. (b) P. J. Stang, D. H. Cao, S. Saito, A. M. Arif. J. Am. Chem. Soc. 117, 6273 (1995);
20. (c) P. J. Stang, D. H. Cao. J. Am. Chem. Soc. 116, 4981 (1994);
21. (d) J. A. Whiteford, P. J. Stang, S. D. Huang. Inorg. Chem. 37, 5595 (1998);
22. (e) P. J. Stang, N. E. Persky, J. Manna. J. Am. Chem. Soc. 119, 4777 (1997);
23. (f) P. J. Stang, B. Olenyuk, D. C. Muddiman, R. D. Smith. Organometallics 16, 3094 (1997).
24. (a) M. Fujita, O. Sasaki, T. Mitsuhashi, T. Fujita, J. Yazaki, K. Yamaguchi, K. Ogura. Chem. Commun. 1535 (1996);
25. (b) M. Fujita, D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi, K. Ogura. Nature 378, 469 (1995);
26. (c) M. Fujita, J. Yazaki, K. Ogura. Tetrahedron Lett. 32, 5589 (1991).
27. B. F. Hoskins, R. Robson. J. Am. Chem. Soc. 112, 1546 (1990).
28. D. J. Iverson, G. Hunter, J. F. Blount, J. R. Damewood Jr., K. Mislow. J. Am. Chem. Soc. 103, 6073 (1981).
29. K. V. Kilway, J. S. Siegel. J. Am. Chem. Soc. 113, 2332 (1991).
30. K. V. Kilway, J. S. Siegel. J. Am. Chem. Soc. 114, 255 (1992).
31. K. V. Kilway, J. S. Siegel. Tetrahedron 57, 3615 (2001).
32. C. Walsdorff, K.-M. Park, J. Oh, K. Kim. Acta Crystallogr., Sect. C 55, 108 (1999).
33. (a) S.-W. Tam-Chang, J. S. Stehouwer, J. Hao. J. Org. Chem. 64, 334 (1999);
34. (b) T. Szabo, B. M. O'Leary, J. Rebek Jr. Angew. Chem., Int. Ed. 37, 3410 (1998);
35. (c) A. P. Bisson, V. M. Lynch, M.-K. C. Monahan, E. V. Anslyn. Angew. Chem., Int. Ed. Engl. 36, 2340 (1997).
36. (a) A. Metzger, V. M. Lynch, E. V. Anslyn. Angew. Chem., Int. Ed. Engl. 36, 862 (1997);
37. (b) D. M. Perreault, L. A. Cabell, E. V. Anslyn. Bioorg. Med. Chem. 5, 1209 (1997).
38. C. Walsdorff, W. Saak, S. Pohl. J. Chem. Res. (S) 282 (1996).
39. (a) T. D. P. Stack, Z. Hou, K. N. Raymond. J. Am. Chem. Soc. 115, 6466 (1993);
40. (b) T. D. P. Stack, T. B. Karpishin, K. N. Raymond. J. Am. Chem. Soc. 114, 1512 (1992).
41. (a) J. Podlaha, I. Císarová, D. Alexander, P. Holy, T. Kraus, J. Závada. Collect. Czech. Chem. Commun. 65, 1587 (2000);
42. (b) M. Nakanishi, T. Kuriyama, H. Yuki. Japan 13096 (1967);
43. Chem. Abstr. 1967, 67, 108458;
44. (c) B. Behnisch, M. Hanack. Synth. Met. 121, 1661 (2001).
45. (a) H. A. Staab, P. Wahl, K.-Y. Kay. Chem. Ber. 120, 541 (1987);
46. (b) H. Suzuki, T. Hanafusa. Bull. Chem. Soc. Jpn. 47, 2625 (1974).
47. S. R. Batten, B. F. Hoskins, R. Robson. New J. Chem. 173 (1998).
48. K. A. Hirsch, S. R. Wilson, J. S. Moore. Chem. Commun. 13 (1998). 23.
49. (a) K. A. Hirsch, S. R. Wilson, J. S. Moore. Inorg. Chem. 36, 2960 (1997);
50. (b) K. A. Hirsch, S. R. Wilson, J. S. Moore. J. Am. Chem. Soc. 119, 10401 (1997).
51. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart. J. Am. Chem. Soc. 107, 3902 (1985).
52. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. A. Keith, G. A. Pettersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, H. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chem, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gompers, R. L. Martin, D. C. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, C. Pople. Gaussian 94, Revision D.3. Gaussian, Inc., Pittsburgh, PA, 1996.
53. (a) G. A. Lawrance. Chem. Rev. 86, 17 (1986);
54. (b) W. Beck, K. Sünkel. Chem. Rev. 88, 1405 (1988).
55. R. W. Turner, E. L. Amma. J. Am. Chem. Soc. 88, 3243 (1966).
56. (a) Z. Otwinowski, W. Minor. Met. Enzymol. 276, 307 (1997);
57. (b) A. L. Spek. J. Appl. Crystallogr. 36, 7 (2003).
58. G. M. Sheldrick. SHELXTL Version 5, Siemens Analytical X-ray Instruments, Madison, WI, 1996.
59. 1ln, a = 14.2377 (4) Å, b = 10.6924 (3) Å, c = 18.0150 (6) Å, β = 107.797 (1)°.
60. Crystallization of a 1:1 mixture of compound 1 and silver hexafluorophosphate from benzene or toluene gives cubic crystals (space group Fd 3, a = 37.3862 (6) Å (from toluene)) which contain spheroidal complexes of silver and 1 where the silver coordination is trigonal planar, and the conformation of 1 is 6-up (illustrated below). However, although the spheroids are well ordered, and the anions show only moderate disorder, the remainder of the unit cell (nearly 60 % of its volume) is comprised of highly disordered silver complexes of an uncertain structure which have compromised the refinement.