Crystal structures of spiroborates derived from 2,2′- dihydroxybiphenyl

Crystal Growth and Design

Volumn 8, Issue 1, 2008, Pages 308-318

  Voisin, Emilie ^a   Maris, Thierry ^a   Wuest, James D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 38549154925     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg700803k     Document Type: Article

References (79)

1. (a) Dunitz, J. D. Chem. Commun. 2003, 545-548.
2. (b) Desiraju, G. R. Nat. Mater. 2002, 1, 77-79.
3. (c) Gavezzotti, A. Acc. Chem. Res. 1994, 27, 309-314.
4. (d) Maddox, J. Nature 1988, 335, 201.
5. Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696-4697.
6. (a) For recent reviews, see Wuest, J. D. Chem. Commun. 2005, 5830-5837.
7. (b) Hosseini, M. W. Acc. Chem. Res. 2005, 38, 313-323.
8. (a) For recent references, see Maly, K. E.; Gagnon, E.; Maris, T.; Wuest, J. D. J. Am. Chem. Soc. 2007, 129, 4306-4322.
9. (b) Roques, N.; Maspoch, D.; Wurst, K.; Ruiz-Molina, D.; Rovira, C.; Veciana, J. Chem. Eur. J. 2006, 12, 9238-9253.
10. (c) Lebel, O.; Maris, T.; Perron, M.-È.; Demers, E.; Wuest, J. D. J. Am. Chem. Soc. 2006, 128, 10372-10373.
11. (d) Sokolov, A. N.; Friščić, T.; MacGillivray, L. R. J. Am. Chem. Soc. 2006, 128, 2806-2807.
12. (e) Pigge, F. C.; Dighe, M. K.; Rath, N. P. Cryst. Growth Des. 2006, 6, 2732-2738.
13. (f) Saha, B. K.; Nangia, A.; Nicoud, J.-F. Cryst. Growth Des. 2006, 6, 1278-1281.
14. (g) Jayaraman, A.; Balasubramaniam, V.; Valiyaveettil, S. Cryst. Growth Des. 2006, 6, 636-642.
15. (h) Suslick, K. S.; Bhyrappa, P.; Chou, J.-H.; Kosal, M. E.; Nakagaki, S.; Smithenry, D. W.; Wilson, S. R. Acc. Chem. Res. 2005, 38, 283-291.
16. (i) Aakeröy, C. B.; Desper, J.; Urbina, J. F. Chem. Commun. 2005, 2820-2822.
17. (j) Braga, D.; Brammer, L.; Champness, N. R. CrystEngComm 2005, 7, 1-19.
18. (k) Sisson, A. L.; del Amo Sanchez, V.; Magro, G.; Griffin, A. M. E.; Shah, S.; Charmant, J. P. H.; Davis, A. P. Angew. Chem., Int. Ed. 2005, 44, 6878-6881.
19. (l) Malek, N.; Maris, T.; Perron, M.-È.; Wuest, J. D. Angew. Chem., Int. Ed. 2005, 44, 4021-4025.
20. (m) Voogt, J. N.; Blanch, H. W. Cryst. Growth Des. 2005, 5, 1135-1144.
21. (n) Lee, S.-O.; Shacklady, D. M.; Horner, M. J.; Ferlay, S.; Hosseini. M. W.; Ward, M. D. Cryst. Growth Des. 2005, 5, 995-1003.
22. (o) Custelcean, R.; Gorbunova, M. G.; Bonnesen, P. V. Chem. Eur. J. 2005, 11, 1459-1466.
23. (p) Moorthy, J. N.; Natarajan, R.; Venugopalan, P. J. Org. Chem. 2005, 70, 8568-8571.
24. (q) Soldatov, D. V.; Moudrakovski, I. L.; Ripmeester, J. A. Angew. Chem., Int. Ed. 2004, 43, 6308-6311.
25. (r) Alshahateet, S. F.; Nakano, K.; Bishop, R.; Craig, D. C.; Harris. K. D. M.; Scudder, M. L. CrystEngComm 2004, 6, 5-10.
26. (a) Nangia, A.; Desiraju, G. R. Top. Curr. Chem. 1998, 198, 57-95.
27. (b) Desiraju. G. R. Angew. Chem., Int. Ed. 1995, 34, 2311-2327.
28. (a) Saied, O.; Maris, T.; Wang, X.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 2005, 127, 10008-10009.
29. (b) Malek, N.; Maris, T.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 2005, 127, 5910-5916.
30. (c) Malek, N.; Maris, T.; Simard, M.; Wuest, J. D. Acta Crystallogr. 2005, E61, o518-o520.
31. (d) Laliberté, D.; Maris, T.; Demers, E.; Helzy, F.; Arseneault, M.; Wuest, J. D. Cryst. Growth Des. 2005, 5, 1451-1456.
32. (e) Laliberté, D.; Maris, T.; Wuest, J. D. Can. J. Chem. 2004, 82, 386-398.
33. (f) Fournier, J.-H.; Maris, T.; Wuest, J. D.; Guo, W.; Galoppini, E. J. Am. Chem. Soc. 2003, 125, 1002-1006.
34. (g) Fournier, J.-H.; Maris, T.; Simard, M.; Wuest, J. D. Cryst. Growth Des. 2003, 3, 535-540.
35. (h) Brunet, P.; Demers, E.; Maris, T.; Enright, G. D.; Wuest, J. D. Angew. Chem., Int. Ed. 2003, 42, 5303-5306.
36. (i) Le Fur, E.; Demers, E.; Maris, T.; Wuest, J. D. Chem. Commun. 2003, 2966-2967.
37. Fournier, J.-H.; Maris, T.; Wuest, J. D. J. Org. Chem. 2004, 69, 1762-1775.
38. Finkelstein, M.; Mayeda, E. A.; Ross, S. D. J. Org. Chem. 1975, 40, 804-805.
39. (a) Shan, Z.; Huang, X.; Zhao, D. Synth. React. Inorg. Met.-Org. Chem. 1990, 30, 33-43.
40. (b) Okamoto, Y.; Kinoshita, T.; Takei, Y.; Matsumoto, Y. Polyhedron 1986, 5, 2051-2057.
41. Alkorta, I.; Picazo, Ó.; Elguero, J. Tetrahedron Asymmetry 2005, 16, 755-760.
42. Green, S.; Nelson, A.; Warriner, S.; Whittaker, B. J. Chem. Soc., Perkin Trans. 2000, 1, 4403-4408.
43. (a) Gloede, J.; Pieper, U.; Habicher, W. D.; Schneider, M. Z. Anorg. Allg. Chem. 2002, 628, 480-487.
44. (b) Kumara Swamy, K. C.; Sreelatha, C.; Day, R. O.; Holmes, J.; Holmes, R. R. Phosphorus, Sulfur, and Silicon 1995, 100, 107-121.
45. (c) Allcock, H. R.; Nugent, T. A.; Smeltz, L. A. Synth. Inorg. Met.-Org. Chem. 1972, 2, 97-104.
46. (d) Silcox, C. M.; Zuckerman, J. J. J. Am. Chem. Soc. 1966, 168-169.
47. (e) Silcox Yoder, C. M.; Zuckerman, J. J. J. Heterocycl. Chem. 1967, 4, 166-167.
48. (f) Zuckerman, J. J. J. Chem. Soc. 1963, 1322-1324.
49. (g) Schwartz, R.; Kuchen, W. Z. Anorg. Allg. Chem. 1955, 279, 84-93.
50. (a) The structures of related borates derived from 2,2′-binaphthol have been reported. Shibasaki, M.; Matsunaga, S. Chem. Soc. Rev. 2006. 35, 269-279.
51. (b) Llewellyn, D. B.; Adamson, D.; Arndtsen, B. A. Org. Lett. 2000, 2, 4165-4168.
52. (c) Periasamy, M.; Venkatraman, L.; Sivakumar, S.; Sampathkumar, N.; Ramanathan, C. R. J. Org. Chem. 1999, 64, 7643-7645.
53. (d) Periasamy, M.; Ramanathan, C. R.; Kumar, N. S. Tetrahedron: Asymmetry 1999, 10, 2307-2310.
54. (e) Ishihara, K.: Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520-10524.
55. For a recently published structure of a substituted derivative of spiroborate 4, see Malkowsky, I. M.; Rommel, C. E.: Fröhlich, R.; Griesbach, U.; Pütter, H.; Waldvogel, S. R. Chem. Eur. J. 2006, 12, 7482-7488.
56. For a related structure, see Katagiri, H.; Miyagawa, T.; Furusho, Y.: Yashima, E. Angew. Chem., Int. Ed. 2006, 45, 1741-1744.
57. For the structure of a lithium complex of spiroborate 4, see Knizek, J.; Nöth, H.; Warchhold, M. Z. Naturforsch. 2006, 61b, 1079-1093.
58. For a recent review of crystal engineering using molecules containing boron, see Maly, K. E.; Malek, N.; Fournier, J.-H.; Rodriguez-Cuamatzi, P.; Maris, T.; Wuest, J. D. Pure Appl. Chem. 2006, 78, 1305-1321.
59. 1H NMR spectroscopy of dissolved samples.
60. Brock, C. P.; Schweizer, W. B.; Dunitz, J. D. J. Am. Chem. Soc. 1991, 113, 9811-9820.
61. (a) Mazaleyrat, J.-P.; Wright, K.; Gaucher, A.; Toulemonde, N.; Dutot, L.; Wakselman, M.; Broxterman, Q. B.; Kaptein, B.; Oancea, S.; Peggion, C.; Crisma, M.; Formaggio, F.; Toniolo, C. Chem.-Eur. J. 2005, 11, 6921-6920.
62. (b) Superchi, S.; Casarini, D.; Laurita, A.; Bavoso, A.; Rosini, C. Angew. Chem., Int. Ed. 2001, 40, 451-454.
63. (c) Carter, R. E.; Dahlqvist, K.-I.; Berntsson, P. Org. Magn. Res. 1977, 9, 44-48.
64. Clegg, W.; Errington, R. J.; Carmalt, C. J. Acta Crystallogr. 1997, C53, 751-753.
65. (a) Malkowsky, I. M.; Fröhlich, R.; Griesbach, U.; Pütter, H.; Waldvogel, S. R. Eur. J. Inorg. Chem. 2006, 1690-1697.
66. (b) Errington, R. J.; Tombul, M.; Walker, G. L. P.; Clegg, W.; Heath, S. L.; Horsburgh, L. J. Chem. Soc., Dalton Trans. 1999, 3533-3534.
67. (a) Xu, Z.; Zhao, C.; Lin, Z. J. Chem. Soc., Perkin Trans. 2000, 2, 2319-2323.
68. (b) Gillespie, R. J.; Bytheway, I.; Robinson, E. A. Inorg. Chem. 1998, 37, 2811-2825.
69. (c) Narasimhamurthy, N.; Manohar, H.; Samuelson, A. G.; Chandrasekhar, J. J. Am. Chem. Soc. 1990, 112, 2937-2941.
70. (a) The ability of C-H bonds to participate in weak hydrogen bonds has been reviewed by Desiraju, G. R. Chem. Commun. 2005, 2995-3001.
71. (b) Desiraju, G. R. Acc. Chem. Res. 2002, 35, 565-573.
72. (c) Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, 1999.
73. The dimensions of a channel in a particular direction correspond to those of an imaginary cylinder that could be passed through the hypothetical open network in the given direction in contact with the van der Waals surface. Such values are inherently conservative because (1) they measure the cross section at the most narrow constriction, and (2) they systematically underestimate the sizes of channels that are not uniform and linear.
74. g is the guest-accessible volume as calculated by PLATON.
75. (a) Spek, A. L. PLATON. A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 2001.
76. (b) van der Sluis, P.; Spek, A. L. Acta Crystallogr. 1990, A46, 194-201.
77. See the Supporting Information for a more detailed description.
78. For a recent reference, see Bovicelli, P.; Antonioletti, R.; Onori, A.; Delogu, G.; Fabbri. D.: Dettori, M. A. Tetrahedron 2006, 62, 635-639."
79. Sheldrick, G. M. SHELXS-97. Program for the Solution of Crystal Structures and SHELXL-97, Program for the Refinement of Crystal Structures: Universität Göttingen: Germany 1997.