Organooxotin cages, {[(n-BuSn)3(μ3-O)(OC6H 4-4-X)3]2[HPO3]4}, X = H, Cl, Br, and I, in double O-capped structures: Halogen-bonding-mediated supramolecular formation

Organometallics

Volumn 24, Issue 21, 2005, Pages 4926-4932

  Chandrasekhar, Vadapalli ^a   Baskar, Viswanathan ^a   Gopal, Kandasamy ^a   Vittal, Jagadese J ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; BONDING; CRYSTAL STRUCTURE; OXYGEN; REACTION KINETICS;

ORGANOOXOTIN CAGES; PHENOLATE OXYGEN; SUPRAMOLECULAR ASSEMBLIES;

ORGANOMETALLICS;

EID: 27144454147     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050269x     Document Type: Article

References (59)

1. (a) Chandrasekhar, V.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1985, 24, 1970.
2. (b) Day, R. O.; Holmes, J. M.; Chandrasekhar, V.; Holmes, R. R. J. Am. Chem. Soc. 1987, 109, 940.
3. (c) Holmes, R. R.; Schmid, C. G.; Chandrasekhar, V.; Day, R. O.; Holmes, J. M. J. Am. Chem. Soc. 1987, 109, 1408.
4. (d) Swamy, K. C. K.; Day, R. O.; Holmes, R. R. J. Am. Chem. Soc. 1987, 109, 5546.
5. (e) Holmes, R. R. Acc. Chem. Res. 1989, 22, 190.
6. (f) Day, R. O.; Chandrasekhar, V.; Swamy, K. C. K.; Holmes, J. M.; Burton, S. D.; Holmes, R. R. Inorg. Chem. 1988, 27, 2887.
7. (a) Chandrasekhar, V.; Nagendran, S.; Bansal, S.; Powell, D. R. Angew. Chem., Int. Ed. 2000, 39,1833.
8. (b) Chandrasekhar, V.; Baskar, V.; Vittal, J. J. J. Am. Chem. Soc. 2003, 125, 2392.
9. (c) Chandrasekhar, V.; Nagendran, S.; Gopal, K.; Steiner, A.; Zacchini, S. Chem. Commun. 2003, 862.
10. (d) Chandrasekhar, V.; Baskar, V.; Boomishankar, R.; Gopal, K.; Zacchini, S.; Bickley, J. F.; Steiner, A. Organometallics 2003, 22, 3710.
11. (a) Chandrasekhar, V.; Baskar, V.; Steiner, A.; Zacchini, S. Organometallics 2004, 23, 1390.
12. (b) Chandrasekhar, V.; Nagendran, S.; Azhakar, R.; Ravikumar, M.; Srinivasan, A.; Ray, K.; Chandrashekar, T. K.; Madhavaiah, C.; Verma, S.; Priyakumar, U. D.; Sastry, G. N. J. Am. Chem. Soc. 2005, 127, 2410.
13. (c) Chandrasekhar, V.; Gopal, K.; Nagendran, S.; Singh, P.; Steiner, A.; Zacchini, S.; Bickley, J. F. Chem. Eur. J. 2005, 11, 5437.
14. (d) Chandrasekhar, V.; Thilagar, P.; Bickley, J. F.; Steiner, A. J. Am. Chem. Soc. 2005, 127, 11556.
15. (a) Swamy, K. C. K.; Said, M. A.; Nagabrahmanandachari, S.; Poojary, D. M.; Clearfield, A. J. Chem. Soc., Dalton Trans. 1998, 1645.
16. (b) Zobel, B.; Costin, J.; Vincent, B. R.; Tiekink, E. R. T.; Dakternieks, D. J. Chem. Soc., Dalton Trans. 2000, 4021.
17. (c) Mehring, M.; Paulus, I.; Zobel, B.; Schürmann, M.; Jurkschat, K.; Duthie, A.; Dakternieks, D. Eur. J. Inorg. Chem. 2001, 153.
18. (d) Beckmann, J.; Dakternieks, D.; Duthie, A.; Mitchell, C. Organometallics 2003, 22, 2161.
19. (a) Xiang, J.; Toyoshima, S.; Orita, A.; Otera, J. Angew. Chem., Int. Ed. 2001, 40, 3670.
20. (b) Otera, J. Acc. Chem. Res. 2004, 37, 288.
21. (c) Kemmer, M.; Biesemans, M.; Gielen, M.; Martins, J. C.; Gramlich, V.; Willem, R. Chem. Eur. J. 2001, 7, 4686.
22. (d) Chaniotakis, N.; Jurkschat, K.; Müller, D.; Perdikaki, K.; Reeske, G. Eur. J. Inorg. Chem. 2004, 2283.
23. (a) García-Zarracino, R.; Ramos-Qui-ones, J.; Höpfl, H. Inorg. Chem. 2003, 42, 3835.
24. (b) Ma, C.; Jiang, Q.; Zhang, R.; Wang, D. J. Chem. Soc., Dalton Trans. 2003, 2975.
25. (c) García-Zarracino, R.; Höpfl, H. Angew. Chem., Int. Ed. 2004, 43, 1507;
26. J. Am. Chem. Soc. 2005, 127, 3120.
27. (d) Prabusankar, G.; Murugavel, R. Organometallics 2004, 23, 5644.
28. (a) Zheng, G.-L.; Ma, J.-F.; Su, J.-M.; Yan, L.-K.; Yang, J.; Li, Y.-Y.; Liu, J.-F. Angew. Chem., Int. Ed. 2004, 43, 2409.
29. (b) Zheng, G.-L.; Ma, J.-F.; Yang, J.; Li, Y.-Y.; Hao, X.-R. Chem. Eur. J. 2004, 10, 3761.
30. (c) Deák, A.; Tárkányi, G. Chem. Commun. 2005, 4074.
31. (a) Chandrasekhar, V.; Nagendran, S.; Baskar, V. Coord. Chem. Rev. 2002, 235, 1.
32. (b) Chandrasekhar, V.; Gopal, K. Appl. Organomet. Chem. 2005, 19, 429.
33. (c) Chandrasekhar, V.; Gopal, K.; Sasikumar, P.; Thirumoorthi, R. Coord. Chem. Rev. 2005, 249, 1745.
34. (a) Eychenne-Baron, C.; Ribot, F.; Sanchez, C. J. Organomet. Chem. 1998, 567, 137.
35. (b) Eychenne-Baron, C.; Ribot, F.; Steunou, N.; Sanchez, C.; Fayon, F.; Biesemans, M.; Martins, J. C.; Willem, R. Organometallics 2000, 19, 1940.
36. (c) Banse, F.; Ribot, F.; Tolédano, P.; Maquet, J.; Sanchez, C. Inorg. Chem. 1995, 34, 6371.
37. (d) Jaumier, P.; Jousscaume, B.; Lahcini, M.; Ribot, F.; Sanchez, C. Chem. Commun. 1998, 369.
38. (e) Dakternieks, D.; Zhu, H.; Tiekink, E. R. T.; Colton, R. J. Organomet. Chem. 1994, 476, 33.
39. (a) Chandrasekhar, V.; Nagendran, S.; Bansal, S.; Cordes, A. W.; Vij, A. Organometallics 2002, 21, 3297.
40. (b) Chandrasekhar, V.; Boomishankar, R.; Singh, S.; Steiner, A.; Zacchini, S. Organometallics 2002, 21, 4575.
41. (c) Chandrasekhar, V.; Boomishankar, R.; Steiner, A.; Bickley, J. F. Organometallics 2003, 22, 3342.
42. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386.
43. (a) Corradi, E.; Meille, S. V.; Messina, M. T.; Metrangolo, P.; Resnati, G. Angew. Chem., Int. Ed. 2000, 39, 1782.
44. (b) Zordan, F.; Brammer, L.; Sherwood, P. J. Am. Chem. Soc. 2005, 127, 5979.
45. (c) Weiss, R.; Schwab, O.; Hampel, F. Chem. Eur. J. 1999, 5, 968, and references therein.
46. (a) Murray-Rust, P.; Motherwell, W. D. S. J. Am. Chem. Soc. 1979, 101, 4374.
47. (b) Ramasubbu, N.; Parthasarathy, R.; Murray-Rust, P. J. Am. Chem. Soc. 1986, 108, 4308.
48. (c) Desiraju, G. R.; Parthasarathy, R. J. Am. Chem. Soc. 1989, 111, 8725.
49. (d) Lommerse, J. P. M.; Stone, A. J.; Taylor, R.; Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108.
50. (e) Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018.
51. (f) Metrangolo, P.; Resnati, G. Chem. Eur. J. 2001, 7, 2511.
52. (g) Caronna, T.; Liantonio, R.; Logothetis, T. A.; Metrangolo, P.; Pilati, T.; Resnati, G. J. Am. Chem. Soc. 2004, 126, 4500.
53. Paulini, R.; Müller, K.; Diederich, F. Angew. Chem., Int. Ed. 2005, 44, 1788.
54. See Supporting Information.
55. (a) Moorthy, J. N.; Venkatakrishnan, P.; Mal, P.; Dixit, S.; Venugopalan, P. Cryst. Growth Des. 2003, 3, 581.
56. (b) Thaimattam, R.; Xue, F.; Sarma, J. A. R. P.; Mak, T. C. W.; Desiraju, G. R. J. Am. Chem. Soc. 2001, 123, 4432, and references therein.
57. Yields are based on the crystals isolated from their reaction mixture.
58. Sheldrick, G. M. SHELX97, Programs for the Solution and Refinement of Crystal Structures; Institut für Anorganische Chemie der Universität Göttingen: Göttingen, Germany, 1998.
59. DIAMOND version 3.0; Crystal Impact GbR: Bonn, Germany, 2004.