Stabilization of molecular LiF and LiFHF inside metallamacrocyclic hosts

Inorganic Chemistry

Volumn 41, Issue 21, 2002, Pages 5466-5474

  Lehaire, Marie Line ^a   Scopelliti, Rosario ^a   Severin, Kay ^a  

^a Institut de chimie moleculaire et biologique Ecole Polytechnique Federale de Lausanne   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; FLUORINE; HYDROGEN; LITHIUM; NITROGEN; OXYGEN; RUTHENIUM;

ANION EXCHANGE; ARTICLE; ATOM; CHEMICAL BINDING; CHEMICAL REACTION; COMPLEX FORMATION; CRYSTAL STRUCTURE; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY ANALYSIS;

EID: 0037152380     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic025749k     Document Type: Article

References (100)

1. (a) Dietrich, B.; Viout, P.; Lehn, J.-M. Macrocyclic Chemistry; VCH: Weinheim, Germany, 1993.
2. (b) Gokel, G. W. Crown Ethers and Cryptands; Royal Society of Chemistry: Cambridge, U.K., 1991.
3. (c) Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening. R. L. Chem. Rev. 1995, 95, 2529-2586.
4. (d) Izatt, R. M.; Bradshaw, J. S.; Pawlak, K.; Bruening, R. L.; Tarbet, B. J. Chem. Rev. 1992, 92, 1261-1354.
5. (e) Izatt, R. M.; Bradshaw, J. S.; Nielsen, S. A.; Larnb,Lamb, J. D.; Christensen, J. A. Cliem.Chem. Rev. 1985, 85, 271-339.
6. (f) Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle. F., Suslick K. S., Eds. Comprehensive Supramolecular Chemistry; Pergamon Press: New York, 1996; Vol. 1.
7. (a) Demsar, A.; Pevec, A.; Golič, L.; Petriček.; Petrič, A.; Roesky, H. W. Chem. Commun. 1998, 1029-1030.
8. (b) Plenio. H.; Diodone, R. J. Am. Chem. Soc. 1996, 118, 356-367.
9. (c) Künzel, A.; Roesky, H. W.; Noltemeyer, M.; Schmidt, H.-G. Chem. Commun. 1995, 2145-2146.
10. (d) Walter, S.; Klingebiel, U. Coord. Chem. Rev. 1994. 130, 481-508.
11. (e) Klingebiel, U.; Meyer, M.; Pieper, U.; Stalke, D. J. Organomet. Chem. 1991, 408, 19-25.
12. 4(LiF)], see ref 2a.
13. Morris, D. F. C. Acta Crystallogr. 1956, 9, 197-198.
14. (a) Emsley, J.; Johnson, D. A. Polyhedron 1986, 5, 1109-1110.
15. (b) Emsley, J. Polyhedron 1985, 4, 489-490.
16. Cram, D. J. Science 1983, 219, 1177-1183.
17. (a) Cram, D. J.; Cram, J. M. Container Molecules and Their Guests: Stoddart, J. F., Ed.; Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, U.K., 1994.
18. (b) Warmuth, R.; Yoon, J. Acc. Chem. Res. 2001, 34, 95-105.
19. (a) Warmuth R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1347.
20. (b) Warmuth, R. Chem. Commun. 1998, 59-60.
21. (a) Warmuth, R. J. Am. Chem. Soc. 2001, 123, 6955-6956
22. (b) Warmuth, R.; Marvel, M. A. Chem. Eur. J. 2001, 7, 1209-1220.
23. (c) Warmuth, R.; Marvel, M. A. Angew. Chem., Int. Ed. 2000, 39, 1117-1119.
24. (a) Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 509-518.
25. (b) Holliday, B. J.; Mirkin, C. A. Angew. Chem., Int. Ed. 2001, 40, 2022-2043.
26. (c) Dinolfo, P. H.; Hupp, J. T. Chem. Mater. 2001, 13, 3113-3125.
27. (d) Swiegers, G. F.; Malefetse, T. J. Chem. Rev. 2000, 100, 3483-3538.
28. (e) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908.
29. (a) Amouri, H.; Rager, M. N.; Cagnol, F.; Vaissermann, J. Angew. Chem., Int. Ed. 2001, 40, 3636-3638.
30. (b) Umemoto, K.; Tsukui, H.; Kusukawa, T.; Biradha, K.; Fujita, M. Angew. Chem., Int. Ed. 2001, 40, 2620-2622.
31. (c) Fochi, F.; Jacopozzi, P.; Wegelius, E.; Rissanen, K.; Cozzini, P.; Marastoni, E.; Fisicaro, E.; Manini, P.; Fokkens, R.; Dalcanale, E. J. Am. Chem. Soc. 2001, 123, 7539-7552.
32. (d) Park, S. J.; Hong, J.-I. Chem. Commun. 2001, 1554-1555.
33. (e) Su, C.-Y.; Cai Y.-P.; Chen, C.-L.; Zhang, H.-X.; Kang, B.-S. J. Chem. Soc., Dalton Trans. 2001, 359-361.
34. (f) Ikeda, A.; Yoshimura, M.; Udzu, H.; Fukuhara, C.; Shinkai, S. J. Am. Chem. Soc. 1999, 121, 4296-4297.
35. (g) Müller, C.: Whiteford, J. A.; Stang, P. J. J. Am. Chem. Soc. 1998, 120, 9827-9837.
36. (h) Ogo, S.; Nakamura, S.; Chen, H.; Isobe, K.; Watanabe, Y.; Fish, R. H. J. Org. Chem. 1998, 63, 7151-7156.
37. (a) Yoshizawa, M.; Kusukawa, T.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. J. Am. Chem. Soc. 2001, 123, 10454-10459.
38. (b) Yoshizawa, M.; Kusukawa, T.; Fujita, M.; Yamaguchi, K. J. Am. Chem. Soc. 2000, 122, 6311-6312.
39. Ziegler, M.; Brumaghim, J. L.; Raymond, K. N. Angew. Chem., Int. Ed. 2000, 39, 4119-4121.
40. (a) Pecoraro, V. L.; Stemmler, A. J.; Gibney, B. R.; Bodwin, J. J.; Wang, H.; Kampf, J. W.; Barwinski, A. Prog. Inorg. Chem. 1997. 45, 83.
41. Mandal, S. K.; Young, G. V.; Que, L., Jr. Inorg. Chem. 2000, 39, 1831-1833.
42. (c) Cutland, A. D.; Malkani, R. G.; Kampf, J. W.; Pecoraro, V. L. Angew. Chem., Int. Ed. 2000, 39, 2689-2692.
43. (d) Saalfrank, R. W.; Löw, N.; Kareth, S.; Seitz, V.; Hample, F.; Stalke, D.; Teichert, M. Angew. Chem., Int. Ed. 1998, 37, 172-175.
44. (e) Saalfrank, R. W.; Bernt, I.; Uller, E.; Hampel, F. Angew. Chem., Int. Ed. 1997, 37, 2482-2485.
45. (f) Caneschi, A.; Cornia, A.; Fabretti, A. C.; Foner, S.; Gatteschi, D.; Grandi, R.; Schenetti, L. Chem. Eur. J. 1996, 2, 1379-1387.
46. (g) Saalfrank, R. W.; Löw, N.; Hampel, F.; Stachel H.-D. Angew. Chem., Int. Ed. Engl. 1996, 35, 2209-2210.
47. (h) Rauter, H.; Hillgreis, E. C.; Erxleben, A.; Lippert, B. J. Am. Chem. Soc. 1994, 116, 616-624.
48. (i) Blake, A. J.; Gould, R. O.; Milne, P. E. Y.; Winpenny, R. E. P. J. Chem. Soc., Chem. Commun. 1991, 1435-1455.
49. (j) Lah, M. S.; Pecoraro, V. L. J. Am. Chem. Soc. 1989, 111, 7258-7259.
50. (k) Lah, M. S.; Kirk, M. L.; Hatfield, W.; Pecoraro, V. L. J. Chem. Soc., Chem. Commun. 1989, 1606-1608.
51. (a) Habereder, T.; Warchhold, M.; Nöth, H.; Severin, K. Angew. Chem., Int. Ed. 1999, 38, 3225-3228.
52. (b) Lang, R.; Polborn, K.; Severin, T.; Severin, K. Inorg. Chim. Acta 1999, 294, 62-67.
53. (c) Lang, R.; Schörwerth, A.; Polborn, K.; Ponikwar, W.; Beck, W.; Severin, T.; Severin, K. Z. Anorg. Allg. Chem. 1999, 625, 1384-1390.
54. (a) Piotrowski, H.; Polborn, K.; Hilt, G.; Severin, K. J. Am. Chem. Soc. 2001. 123, 2699-2700.
55. (b) Piotrowski, H.; Hilt, G.; Schulz, A.; Mayer, P.; Polborn, K.; Severin, K. Chem. Eur. J. 2001, 7, 3196-3208.
56. Lehaire, M.-L.; Scopelliti, R.; Piotrowski, H.; Severin, K. Angew. Chem., Int. Ed. 2002, 41, 1419-1422.
57. Piotrowski, H.; Severin, K. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4997-5000.
58. Sharma, R. K.; Fry, J. L. J. Org. Chem. 1983, 48, 2112-2114.
59. Oxford Diffraction Ltd., Abingdon, Oxfordshire, U.K., 2001.
60. Otwinowski, Z.; Minor, W. Methods in Enzymology; Carter, C. W., Jr., Sweet, R. M., Eds.; Academic Press: New York, 1997; Vol. 276: Macromolecular Crystallography, Part A, pp 307-326.
61. Blessing, R. H. Acta Crystallogr. A 1995, 51, 33-38.
62. Walker, N.; Stuart, D. Acta Crystallogr. A 1983, 39, 158-166.
63. Sheldrick, G. M. Acta Crystallogr. A 1990, 46, 467-473.
64. Sheldrick, G. M. Bruker AXS, Inc.: Madison, Wisconsin, 1997.
65. ORTEP 3 for Windows, version 1.074. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
66. Li, J. J.; Li, W.; Sharp, P. R. Inorg. Chem. 1996, 35, 604-613.
67. Strong hydrogen bonds are typically characterized by A⋯B separations that are at least 0.25 Å less than the sum of the van der Waals radii. See: Hibbert, F.; Emsey. J. Adv. Phys. Org. Chem. 1990, 26, 255-379.
68. (a) Boenigk, D.; Mootz, D. J. Am. Chem. Soc. 1988, 110, 2135-2139.
69. (b) Farnham, W. B.; Dixon, D. A.; Middleton, W. J.; Calabrese, J. C.; Harlow, R. L.; Whiteney, J. F.; Jones, G. A.; Guggenberger, L. J. J. Am. Chem. Soc. 1987, 109, 476-483.
70. (c) Emsley, J. Chem. Soc. Rev. 1980, 9, 91-124.
71. (d) Ault, B. S. Acc. Chem. Res. 1982, 15, 103-109.
72. (e) Ibers, J. J. Chem. Phys. 1964, 40, 402-404.
73. (f) McGaw, B. L.; Ibers, J. A. J. Chem. Phys. 1963, 39, 2677-2684.
74. (g) Freel, L. K.; Rinn, H. W. Acta Crystallogr. 1962, 15, 286-286.
75. (h) McDonald, T. R. R. Acta Crystallogr. 1960, 13, 113-124.
76. Wenthold, P. G.; Squires, R. R. J. Phys. Chem. 1995, 99, 2002-2005.
77. Kawahara, S.-I.; Uchimaru, T.; Taira, K Chem. Phys. 2001, 273, 207-216 and references cited therein.
78. (a) Petera, S. A.; Bartlett, R. J. J. Am. Chem. Soc. 2000, 122, 1231-1232.
79. (b) Ludman, C. J.; Waddington, T. C.; Pang, E. K. C.; Smith, J. A. S. J. Chem. Soc., Faraday Trans. 2 1977, 73, 1003-1014.
80. (c) Cousseau, J.; Gouin, L.; Pang, E. K. C.; Smith, J. A. S. J. Chem. Soc., Faraday Trans. 2 1977, 73, 1015-1019.
81. (d) Martin, J. S.; Fujiwara, F. Y. J. Am. Chem. Soc. 1974, 196, 7632-7637.
82. (e) Martin, J. S.; Fujiwara, F. Y. Can. J. Chem. 1971, 49, 3071-3073.
83. (a) Kirkham, M. S.; Mahon, M. F.; Whittlesey, M. K. Chem. Commun. 2001, 813-814.
84. (b) Jasim, N. A.; Perutz, R. N.; Foxon, S. P.; Walton, P. H. J. Chem. Soc., Dalton Trans. 2001. 1676-1685.
85. (c) Roe, D. C.; Marshall, W. J., Davidson, F.; Soper, P. D.; Grushin, V. V. Organometallics 2000, 19, 4575-4582.
86. (d) Jasim, N. A.; Perutz, R. N. J. Am. Chem. Soc. 2000, 122, 8685-8693.
87. (e) Archibald, S. J.; Braun, T.; Gaunt, J. A.; Hobson, J. E.; Perutz, R. N. J. Chem. Soc., Dalton Trans. 2000, 2013-2018.
88. (f) Braun, T.; Foxon, S. P.; Perutz, R. N., Walton, P. H. Angew. Chem., Int. Ed. 1999, 38, 3326-3329.
89. (g) Gil-Rubio, J.; Weberndörfer, B.; Werner, H. J. Chem. Soc., Dalton Trans. 1999, 1437-1444.
90. (h) Murphy, V. J.; Rabinovich, D.; Hascall, T.; Klooster, W. T.; Koetzle, T. F.; Parkin, G. J. Am. Chem. Soc. 1998, 120, 4372-4387.
91. (i) Whittlesey, M. K.; Perutz, R. N.; Greener, B.; Moore, M. H. Chem. Commun. 1997, 187-188.
92. (j) Murphy, V. J.; Hascall, T.; Chen, J. Y.; Parkin, G. J. Am. Chem. Soc. 1996, 118, 7428-7429.
93. The fluorine bound directly to the lithium is referred to as proximal, and the fluorine bound via the hydrogen bond as distal.
94. Bach, R. D.; Dmitrenko, O.; Glukhovtsev, M. N. J. Am. Chem. Soc. 2001, 123, 7134-7145.
95. Wells, A. F. Structural Inorganic Chemistry, 4th ed.; Claredon Press: Oxford, U.K., 1975; p 375.
96. Rowland, R. S.; Taylor, R. J. Chem. Phys. 1996, 100, 7384-7391.
97. δ- interactions, see: (a) Güizado-Rodriguez, M.; Ariza-Castolo, A.; Merino, G.; Vela, A.; Nöth, H.; Bakhmutov, V. I.; Contreras. R. J. Am. Chem. Soc. 2001, 123, 9144-9152. (b) Gale, P. A.; Hursthouse, M. B.; Light, M. E.; Sessler, J. L.; Warriner, C. N.; Zimmerman, R. S. Tetrahedron Lett. 2001, 42, 6759-6762. (c) Corey, E. J.; Rhode, J. J.; Fischer, A.; Azimioara, M. D. Tetrahedron Lett. 1997, 38, 33-36. (d) Farnham, W. B.; Roe, D. C.; Dixon, D. A.; Calabrese J. C.; Harlow, R. L. J. Am. Chem. Soc. 1990, 112, 7707-7718.
98. δ- interactions, see: (a) Güizado-Rodriguez, M.; Ariza-Castolo, A.; Merino, G.; Vela, A.; Nöth, H.; Bakhmutov, V. I.; Contreras. R. J. Am. Chem. Soc. 2001, 123, 9144-9152. (b) Gale, P. A.; Hursthouse, M. B.; Light, M. E.; Sessler, J. L.; Warriner, C. N.; Zimmerman, R. S. Tetrahedron Lett. 2001, 42, 6759-6762. (c) Corey, E. J.; Rhode, J. J.; Fischer, A.; Azimioara, M. D. Tetrahedron Lett. 1997, 38, 33-36. (d) Farnham, W. B.; Roe, D. C.; Dixon, D. A.; Calabrese J. C.; Harlow, R. L. J. Am. Chem. Soc. 1990, 112, 7707-7718.
99. δ- interactions, see: (a) Güizado-Rodriguez, M.; Ariza-Castolo, A.; Merino, G.; Vela, A.; Nöth, H.; Bakhmutov, V. I.; Contreras. R. J. Am. Chem. Soc. 2001, 123, 9144-9152. (b) Gale, P. A.; Hursthouse, M. B.; Light, M. E.; Sessler, J. L.; Warriner, C. N.; Zimmerman, R. S. Tetrahedron Lett. 2001, 42, 6759-6762. (c) Corey, E. J.; Rhode, J. J.; Fischer, A.; Azimioara, M. D. Tetrahedron Lett. 1997, 38, 33-36. (d) Farnham, W. B.; Roe, D. C.; Dixon, D. A.; Calabrese J. C.; Harlow, R. L. J. Am. Chem. Soc. 1990, 112, 7707-7718.
100. δ- interactions, see: (a) Güizado-Rodriguez, M.; Ariza-Castolo, A.; Merino, G.; Vela, A.; Nöth, H.; Bakhmutov, V. I.; Contreras. R. J. Am. Chem. Soc. 2001, 123, 9144-9152. (b) Gale, P. A.; Hursthouse, M. B.; Light, M. E.; Sessler, J. L.; Warriner, C. N.; Zimmerman, R. S. Tetrahedron Lett. 2001, 42, 6759-6762. (c) Corey, E. J.; Rhode, J. J.; Fischer, A.; Azimioara, M. D. Tetrahedron Lett. 1997, 38, 33-36. (d) Farnham, W. B.; Roe, D. C.; Dixon, D. A.; Calabrese J. C.; Harlow, R. L. J. Am. Chem. Soc. 1990, 112, 7707-7718.