Benzene-, Pyrrole-, and Furan-Containing Diametrically Strapped Calix[4]pyrroles—An Experimental and Theoretical Study of Hydrogen-Bonding Effects in Chloride Anion Recognition†
Dae-Wi Yoon Dr.
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712 (USA), Fax: (+1) 512-471-7550
Search for more papers by this authorDustin E. Gross
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712 (USA), Fax: (+1) 512-471-7550
Search for more papers by this authorVincent M. Lynch Dr.
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712 (USA), Fax: (+1) 512-471-7550
Search for more papers by this authorJonathan L. Sessler Prof.
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712 (USA), Fax: (+1) 512-471-7550
Search for more papers by this authorBenjamin P. Hay Dr.
Chemical Sciences Division, Oak Ridge National Laboratory, Oak Ridge, TN 37830-6119 (USA)
Search for more papers by this authorChang-Hee Lee Prof.
Department of Chemistry and Vascular System Research Center, Kangwon National University, Chun-Chon 200-701 (Korea)
Search for more papers by this authorDae-Wi Yoon Dr.
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712 (USA), Fax: (+1) 512-471-7550
Search for more papers by this authorDustin E. Gross
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712 (USA), Fax: (+1) 512-471-7550
Search for more papers by this authorVincent M. Lynch Dr.
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712 (USA), Fax: (+1) 512-471-7550
Search for more papers by this authorJonathan L. Sessler Prof.
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712 (USA), Fax: (+1) 512-471-7550
Search for more papers by this authorBenjamin P. Hay Dr.
Chemical Sciences Division, Oak Ridge National Laboratory, Oak Ridge, TN 37830-6119 (USA)
Search for more papers by this authorChang-Hee Lee Prof.
Department of Chemistry and Vascular System Research Center, Kangwon National University, Chun-Chon 200-701 (Korea)
Search for more papers by this authorThis work was supported by the NIH (grant GM 58908 to J.L.S.), the Korea Research Foundation Grant funded by the Korean Government (MOEHRD) (KRF-2006-214-C00047 to D.-W.Y.), and the Korea Science and Engineering Foundation (grant no. R01-2006-000-10001-0 to C.-H.L.), and B.P.H. acknowledges support from the Division of Chemical Sciences, Geosciences, and Biosciences, Office of Basic Energy Sciences, US Department of Energy (DOE) under contract number DE-AC05-00OR22725 with Oak Ridge National Laboratory (managed by UT-Battelle, LLC).
Graphical Abstract
Weak but important: The chloride anion binding properties of diametrically strapped calixpyrroles bearing benzene (see structure), pyrrole, and furan moieties in the strap have been studied in the solid state, in solution, and through theoretical analyses. The results obtained provide support for the notion that CH⋅⋅⋅Cl− hydrogen bonds are significant and contribute substantially to the Cl− binding energetics.
Supporting Information
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References
- 1M. Nishio in Encyclopedia of Supramolecular Chemistry (Ed.: ), Marcel Dekker, New York, 2004, pp. 1576–1585.
- 2
- 2aK. Sato, S. Arai, T. Yamagishi, Tetrahedron Lett. 1999, 40, 5219–5222;
- 2bE. Alcalde, C. Alvarez-Rua, S. Garcia-Granda, E. Garcia-Rodriguez, N. Mesquida, L. Perez-Garcia, Chem. Commun. 1999, 295–296;
- 2cH. Ihm, S. Yun, H. G. Kim, J. K. Kim, K. S. Kim, Org. Lett. 2002, 4, 2897–2900;
- 2dS. K. Kim, B. G. Kang, H. S. Koh, Y. J. Yoon, S. J. Jung, B. Jeong, K.-D. Lee, J. Yoon, Org. Lett. 2004, 6, 4655–4658;
- 2eK. Chellappan, N. J. Singh, I.-C. Hwang, J. W. Lee, K. S. Kim, Angew. Chem. 2005, 117, 2959–2963;
10.1002/ange.200500119 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 2899–2903;
- 2fW. W. H. Wong, M. S. Vickers, A. R. Cowley, R. L. Paul, P. D. Beer, Org. Biomol. Chem. 2005, 3, 4201–4208;
- 2gS. In, S. J. Cho, J. Kang, Supramol. Chem. 2005, 17, 443–446;
- 2hJ. Yoon, S. K. Kim, N. J. Singh, K. W. Kim, Chem. Soc. Rev. 2006, 35, 355–360;
- 2iV. Amendola, M. Boiocchi, B. Colasson, L. Fabbrizzi, M.-J. Rodriguez Douton, F. Ugozzoli, Angew. Chem. 2006, 118, 7074–7078;
10.1002/ange.200602598 Google ScholarAngew. Chem. Int. Ed. 2006, 45, 6920–6924;
- 2jT. Fahlbusch, M. Frank, J. Schatz, H. Schmaderer, Eur. J. Org. Chem. 2006, 1899–1903;
- 2kW. J. Belcher, M. Fabre, T. Farhan, J. W. Steed, Org. Biomol. Chem. 2006, 4, 781–786;
- 2lK. Sato, Y. Sadamitsu, S. Arai, T. Yamagishi, Tetrahedron Lett. 2007, 48, 1493–1496.
- 3
- 3aM. A. French, S. Ikuta, P. Kebarle, Can. J. Chem. 1982, 60, 1907–1918;
- 3bJ. W. Larson, T. B. McMahon, J. Am. Chem. Soc. 1984, 106, 517–521;
- 3cM. Albertí, A. Castro, A. Lagana, M. Moix, F. Pirani, D. Cappelletti, Eur. Phys. J. D 2006, 38, 185–191;
- 3dH. Schneider, K. M. Vogelhuber, F. Schinte, J. M. Weber, J. Am. Chem. Soc. 2007, 129, 13022–13026;
- 3eS. S. Zhu, H. Staats, K. Brandhorst, J. Grunnenberg, F. Gruppi, E. Dalcanale, A. Lutzen, K. Rissanen, C. A. Schalley, Angew. Chem. 2008, 120, 800–804; Angew. Chem. Int. Ed. 2008, 47, 788–792.
- 4C.-H. Lee, H.-K. Na, D.-W. Yoon, D.-H. Won, W.-S. Cho, V. M. Lynch, S. V. Shevchuk, J. L. Sessler, J. Am. Chem. Soc. 2003, 125, 7301–7306.
- 5
- 5aS. O. Kang, D. VanderVelde, D. Powell, K. Bowman-James, J. Am. Chem. Soc. 2004, 126, 12272–12273;
- 5bI. E. D. Vega, P. A. Gale, M. E. Light, S. J. Loeb, Chem. Commun. 2005, 4913–4915;
- 5cH. Maeda, Y. Kusunose, Chem. Eur. J. 2005, 11, 5661–5666;
- 5dT. Zielinski, M. Kedziorek, J. Jurczak, Chem. Eur. J. 2008, 14, 838–846.
- 6aQ.-Y. Chen, C.-F. Chen, Tetrahedron Lett. 2004, 45, 6493;
- 6bJ. Y. Kwon, Y. J. Jang, S. K. Kim, K. H. Lee, J. S. Kim, J. Yoon, J. Org. Chem. 2004, 69, 5155–5157;
- 6cC. Fujimoto, Y. Kusunose, H. Maeda, J. Org. Chem. 2006, 71, 2389–2394;
- 6dR. Nishiyabu, M. A. Palacios, W. Dehaen, P. Anzenbacher, Jr., J. Am. Chem. Soc. 2006, 128, 11496–11504.
- 7Y. Li, A. H. Flood, Angew. Chem. 2008, 120, 2689–2692; Angew. Chem. Int. Ed. 2008, 47, 2649–2652.
- 8
- 8aC. A. Ilioudis, D. A. Tocher, J. W. Steed, J. Am. Chem. Soc. 2004, 126, 12395–12402;
- 8bM. J. Chmielewski, M. Charon, J. Jurczak, Org. Lett. 2004, 6, 3501–3504.
- 9B. P. Hay, V. S. Bryantsev, Chem. Commun. 2008, DOI: .
- 10
- 10aK. Hiraoka, S. Mizuse, S. Yamabe, Chem. Phys. Lett. 1988, 147, 174–178;
- 10bZ. M. Loh, R. L. Wilson, D. A. Wild, E. J. Bieske, A. Zehnacker, J. Chem. Phys. 2003, 119, 9559–9567;
- 10cJ. A. Ortuno, R. Exposito, C. Sanchez-Pedreno, M. I. Albero, A. Espinosa, Anal. Chim. Acta 2004, 525, 231–237;
- 10dP. Botschwina, R. Oswald, V. Dyczmons, Int. J. Mass Spectrom. 2007, 267, 308–314.
- 11
- 11aV. S. Bryantsev, B. P. Hay, J. Am. Chem. Soc. 2005, 127, 8282–8283;
- 11bV. S. Bryantsev, B. P. Hay, Org. Lett. 2005, 7, 5031–5034;
- 11cO. B. Berryman, V. S. Bryantsev, D. P. Stay, D. W. Johnson, B. P. Hay, J. Am. Chem. Soc. 2007, 129, 48–58.
- 12C.-S. Zuo, J.-M. Quan, Y.-D. Wu, Org. Lett. 2007, 9, 4219–4222.
- 13
- 13aD.-W. Yoon, H. Hwang, C.-H. Lee, Angew. Chem. 2002, 114, 1835–1837;
Angew. Chem. Int. Ed. 2002, 41, 1757–1759;
10.1002/1521-3773(20020517)41:10<1757::AID-ANIE1757>3.0.CO;2-0 CAS PubMed Web of Science® Google Scholar
- 13bC.-H. Lee, H. Miyaji, D.-W. Yoon, J. L. Sessler, Chem. Commun. 2008, 24–34.
- 14
- 14aP. A. Gale, J. L. Sessler, V. Kral, V. Lynch, J. Am. Chem. Soc. 1996, 118, 5140–5141;
- 14bJ. L. Sessler, D. E. Gross, W.-S. Cho, V. M. Lynch, F. P. Schmidtchen, G. W. Bates, M. E. Light, P. A. Gale, J. Am. Chem. Soc. 2006, 128, 12281–12288.
- 15T. J. Donohoe, C. E. Headley, R. P. C. Cousins, A. Cowley, Org. Lett. 2003, 5, 999–1002.
- 16The crystal data and experimental details for the structural refinement of 3, 3⋅Cl, and 4⋅2 MeOH are provided in the Supporting Information. CCDC-682547 (3), CCDC-682548 (3⋅Cl), and CCDC-682549 (4⋅2 MeOH) 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.
- 17
- 17aJ. Sunner, K. Nishizawa, P. Kebarle, J. Phys. Chem. 1981, 85, 1814–1820;
- 17bG. J. C. Paul, P. Kebarle, J. Am. Chem. Soc. 1991, 113, 1148–1154.
- 18K. Hiraoka, T. Mizuno, T. Iino, D. Eguchi, S. Yamabe, J. Phys. Chem. A 2001, 105, 4887–4893.
- 19E. J. Bylaska et al., “NWChem, A Computational Chemistry Package for Parallel Computers, Version 5.0” (2006), Pacific Northwest National Laboratory, Richland, Washington 99352-0999, USA. See the Supporting Information for the full citation.
- 20Whereas this analysis provides a quantitative measure of the chloride affinity offered by each binding configuration, we recognize that it does not account for other contributions to the overall binding affinity, such as conformational reorganization that may occur prior to binding or the influence of solvation.
