Abstract: Angewandte Chemie International EditionVolume 45, Issue 12 p. 1921-1925 Communication Trapped Bifluoride† Sung Ok Kang Dr., Sung Ok Kang Dr. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA, Fax: (+1) 785-864-5396Search for more papers by this authorDouglas Powell Dr., Douglas Powell Dr. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA, Fax: (+1) 785-864-5396Search for more papers by this authorVictor W. Day Dr., Victor W. Day Dr. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA, Fax: (+1) 785-864-5396Search for more papers by this authorKristin Bowman-James Prof., Kristin Bowman-James Prof. [email protected] Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA, Fax: (+1) 785-864-5396Search for more papers by this author Sung Ok Kang Dr., Sung Ok Kang Dr. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA, Fax: (+1) 785-864-5396Search for more papers by this authorDouglas Powell Dr., Douglas Powell Dr. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA, Fax: (+1) 785-864-5396Search for more papers by this authorVictor W. Day Dr., Victor W. Day Dr. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA, Fax: (+1) 785-864-5396Search for more papers by this authorKristin Bowman-James Prof., Kristin Bowman-James Prof. [email protected] Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA, Fax: (+1) 785-864-5396Search for more papers by this author First published: 06 March 2006 https://doi.org/10.1002/anie.200504066Citations: 137 † We thank the National Science Foundation for support of this work (CHE-0316623) and for purchase of the X-ray diffractometer (CHE-0079282). Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Graphical Abstract The quest is over: A tricyclic amide-based anion receptor has been synthesized by connecting two monocyclic precursors. The receptor is highly selective for the binding of the elusive bifluoride anion HF2−, and the adduct represents the first structural example of an encapsulated bifluoride. The bifluoride lies midway between the two macrocycles making up the tricycle and is held by four hydrogen-bonding contacts with the macrocyclic amides. References 1J.-M. Lehn, E. Sonveaux, A. K. Willard, J. Am. Chem. Soc. 1978, 100, 4914– 4916. 2R. J. Motekaitis, A. E. Martell, I. Murase, Inorg. Chem. 1986, 25, 938– 944. 3R. J. Motekaitis, A. E. Martell, I. Murase, J.-M. Lehn, M. W. Hosseini, Inorg. Chem. 1988, 27, 3630– 3636. 4 4aS. Mason, J. M. Llinares, M. Morton, T. Clifford, K. Bowman-James, J. Am. Chem. Soc. 2000, 122, 1814– 1815; 4bJ. A. Aguilar, T. Clifford, A. Danby, J. M. Llinares, S. Mason, E. García-España, K. Bowman-James, Supramol. Chem. 2001, 13, 405– 417; 4cM. A. Hossain, J. M. Llinares, S. Mason, P. Morehouse, D. Powell, K. Bowman-James, Angew. Chem. 2002, 114, 2441– 2444; Angew. Chem. Int. Ed. 2002, 41, 2335– 2338; 4dM. A. Hossain, P. Morehouse, D. Powell, K. Bowman-James, Inorg. Chem. 2005, 44, 2143– 2149. 5 5aS. O. Kang, J. M. Llinares, D. Powell, D. VanderVelde, K. Bowman-James, J. Am. Chem. Soc. 2003, 125, 10152– 10153; 5bS. O. Kang, D. VanderVelde, D. Powell, K. Bowman-James, J. Am. Chem. Soc. 2004, 126, 12272– 12273; 5cS. O. Kang, D. Powell, K. Bowman-James, J. Am. Chem. Soc. 2005, 127, 13478– 13479. 6 6aM. A. Hossain, J. M. Llinares, D. Powell, K. Bowman-James, Inorg. Chem. 2001, 40, 2936– 2937; 6bM. A. Hossain, S. O. Kang, D. Powell, K. Bowman-James, Inorg. Chem. 2003, 42, 1397– 1399. 7 7aG. Das, P. Tripathi, A Tripathi, P. K. Bharadwaj, Tetrahedron 2000, 56, 1501– 1504; 7bP. Lipkowski, D. T. Gryko, J. Jurczak, J. Lipkowski, Tetrahedron Lett. 1998, 39, 3833– 3836. 8 8aA. P. Davis, R. S. Wareham, Angew. Chem. 1998, 110, 2397– 2401; Angew. Chem. Int. Ed. 1998, 37, 2270– 2273; 8bA. P. Davis, R. S. Wareham, Angew. Chem. 1999, 111, 3160– 3179; Angew. Chem. Int. Ed. 1999, 38, 2978– 2996; 8cG. Lecollinet, A. P. Dominey, T. Velasco, A. P. Davis, Angew. Chem. 2002, 114, 4267– 4270; Angew. Chem. Int. Ed. 2002, 41, 4093– 4096; 8dE. Klein, M. P. Crump, A. P. Davis, Angew. Chem. 2004, 116, 302– 306; Angew. Chem. Int. Ed. 2005, 44, 298– 302. 9X-ray data for nBu4N+[1(FHF−)]⋅3 H2O: C64H103F2N17O11, Mr=1324.63, crystal dimensions 0.36×0.30×0.30 mm3, orthorhombic, space group C2221, a=14.611(2), b=17.121(2), c=28.675(3) Å, α=β=γ=90°, V=7173(2) Å3, Z=4, ρcalcd=1.227 g cm−3, T=100(2) K, F(000)=2848, μ(MoKα)=0.089 mm−1, 10 514 (Rint=0.043) independent reflections (43 041 measured), R1 (unweighted, based on F)=0.074 for 8546 "observed" reflections having I>2 σ(I) and 2 θ(MoKα) <60.20°; R1 (unweighted, based on F)=0.084, wR2 (weighted, based on F2)=0.221 and GOF (on F2)=1.020 for all 10 514 independent reflections having 2 θ(MoKα)<60.20°. X-ray data for 1⋅6 H2O: C48H72N16O14, Mr=1097.22, crystal dimensions 0.36×0.34×0.10 mm3, monoclinic, space group C2/c, a=17.116(2), b=14.949(2), c=22.082(3) Å, α=γ=90°, β=106.782(3), V=5409(1) Å3, Z=4, ρcalcd=1.347 g cm−3, T=100(2) K, F(000)=2336, μ(MoKα)=0.101 mm−1, 7867 (Rint=0.028) independent absorption-corrected reflections (30 720 measured), R1 (unweighted, based on F)=0.049 for 6680 "observed" reflections having I>2 σ(I) and 2 θ(MoKα)<60.11°; R1 (unweighted, based on F)=0.057, wR2 (weighted, based on F2)=0.132 and GOF (on F2)=1.021 for all 7867 independent absorption-corrected reflections having 2 θ(MoKα)<60.11°. CCDC-289348 and CCDC-289349 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. 10 10aR. K. Sharma, J. L. Fry, J. Org. Chem. 1983, 48, 2112– 2114; 10bD. P. Cox, J. Terpinski, W. Lawrynowicz, J. Org. Chem. 1984, 49, 3216– 3219; 10cK. O. Christe, W. W. Wilson, R. D. Wilson, R. Bau, J. A. Feng, J. Am. Chem. Soc. 1990, 112, 7619– 7625; 10dF. Y. Fujiwara, J. S. Martin, J. Am. Chem. Soc. 1974, 96, 7625– 7631; 10eJ. S. Martin, F. Y. Fujiwara, J. Am. Chem. Soc. 1974, 96, 7632– 7637; 10fH. Sun, S. G. DiMagno, J. Am. Chem. Soc. 2005, 127, 2050– 2051. 11A. M. Costere, M. J. Bañuls, M. J. Aurell, M. D. Ward, S. Argent, Tetrahedron 2004, 60, 9471– 9478. 12 12aD. Esteban-Gómez, L. Fabbrizzi, M. Licchelli, J. Org. Chem. 2005, 70, 5717– 5720; 12bM. Boiocchi, L. D. Boca, D. E. Gómez, L. Fabbrizzi, M. Licchelli, E. Monzani, J. Am. Chem. Soc. 2004, 126, 16507– 16514. 13 13aT. Gunnlaugsson, P. E. Kruger, P. Jensen, F. M. Pfeffer, G. M. Hussey, Tetrahedron Lett. 2003, 44, 8909– 8913; 13bF. M. Pfeffer, T. Gunnlaugsson, P. Jensen, P. E. Kruger, Org. Lett. 2005, 7, 5357– 5360; 13cT. Gunnlaugsson, P. E. Kruger, P. Jensen, J. Tierney, H. D. P. Ali, G. M. Hussey, J. Org. Chem. 2005, 70, 10875– 10878. 14 14aS. Camiolo, P. A. Gale, M. B. Hursthouse, M. E. Light, A. J. Shi, Chem. Commun. 2002, 758– 759; 14bP. A. Gale, K. Navakhun, S. Camiolo, M. E. Light, M. B. Hursthouse, J. Am. Chem. Soc. 2002, 124, 11228– 11229; 14cS. Camiolo, P. A. Gale, M. B. Hursthouse, M. E. Light, Org. Biomol. Chem. 2003, 1, 741– 744. 15M. Hynes, J. Chem. Soc. Dalton Trans. 1993, 311– 312. Citing Literature Supporting Information Supporting information for this article (including details of the synthesis of the precursors to 1) is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2006/z504066_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume45, Issue12March 13, 2006Pages 1921-1925 ReferencesRelatedInformation
Publication Year: 2006
Publication Date: 2006-03-06
Language: en
Type: article
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