Electron density shift in imidazolium derivatives upon complexation with cucurbit[6]uril

Chemistry - A European Journal

Volumn 15, Issue 28, 2009, Pages 6926-6931

  Kolman, Viktor ^a   Marek, Radek ^a   Strelcova, Zora ^a   Kulhanek, Petr ^a   Necas, Marek ^a   Svec, Jan ^a   Sindelar, Vladimir ^a  

^a MASARYK UNIVERSITY   (Czech Republic)

Author keywords

Cucurbiturils; Hostguest systems; Ionic liquids, supramolecular chemistry

Indexed keywords

1H-NMR SPECTRA; ALKYL SUBSTITUENT; AROMATIC RINGS; BINDING MODES; CUCURBIT[6]URIL; CUCURBITURILS; ELECTRON DENSITIES; GUEST MOLECULES; H NMR SPECTRA; HOSTGUEST SYSTEMS; IMIDAZOLIUM; KEY ISSUES; SUPRAMOLECULAR INTERACTIONS;

ALKYLATION; BINDING ENERGY; COMPLEXATION; IONIZATION OF LIQUIDS; MACROMOLECULES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUPRAMOLECULAR CHEMISTRY;

IONIC LIQUIDS;

BRIDGED COMPOUND; CUCURBIT(6)URIL; IMIDAZOLE DERIVATIVE; IONIC LIQUID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

BRIDGED COMPOUNDS; ELECTRONS; IMIDAZOLES; IONIC LIQUIDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR;

EID: 67650496420     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900570     Document Type: Article

References (35)

1. a) J. W. Lee, S. Samal, N. Selvapalam, H.-J. Kim, K. Kim, Acc. Chem. Res. 2003, 36, 621-630;
2. b)J. Lagona, P. Mukhopadhyay, S. Chakrabarti, L. Isaacs, Angew. Chem. 2005, 117, 4922-4949;
3. Angew. Chem. Int. Ed. 2005, 44, 4844-4870.
4. W. A. Freeman, W. L. Mock, N.-Y. Shih, J. Am. Chem. Soc. 1981, 103, 7367-7368.
5. a) W. L. Mock, N.-Y. Shih, J. Org. Chem. 1983, 48, 3618-3619;
6. b) W. L. Mock, N.-Y. Shih, J. Org. Chem. 1986, 51, 4440-4446;
7. W. L. Mock, N.-Y. Shih, J. Am. Chem. Soc. 1988, 110, 4706-4710;
8. W. L. Mock, N.-Y. Shih, J. Am. Chem. Soc. 1989, 111, 2697-2699.
9. a) H. Isobe, N. Tomita, J. W. Lee, H.-J. Kim, K. Kim, E. Nakamura, Angew. Chem. 2000, 112, 4427-4430;
10. Angew. Chem. Int. Ed. 2000, 39, 4257-4260;
11. b) H. Isobe, S. Sota, J. W. Lee, H.-J. Kim, K. Kim, E. Nakamura, Chem. Commun. 2005, 1549-1551.
12. Y. Tan, S. Choi, J. W. Lee, Y. H. Ko, K. Kim, Macromolecules 2002, 35, 7161-7165.
13. C. Márquez, R. R. Hudgins, W. M. Nau, J Am. Chem. Soc. 2004, 126, 5806-5816.
14. H.-J. Buschmann, L. Mutihac, R.-C. Mutihac, E. Schollmeyer, Thermochim. Acta 2005, 430, 79-82.
15. H.-J. Buschmann, E. Schollmeyer, L. Mutihac, Thermochim. Acta 2003, 399, 203-208.
16. R. Wang, L. Juan, D. H. Macartney, Chem. Commun. 2006, 2908-2910.
17. L. Leclercq, N. Noujeim, S. H. Sanon, A. R. Schmitzer, J. Phys. Chem. B 2008, 112, 14176-14184.
18. Ionic Liquids in Synthesis (Eds.: T. Welton, P. Wasserscheid), Wiley VCH, Weinheim, 2002.
19. P. J. Dyson, T. J. Geldbach in Metal Catalysed Reactions in Ionic Liquids, Springer, New York, 2006.
20. Ionic Liquids in Polymer Systems, Vol. 913 of ACS Symposium Series (Eds.: Brazel, C. S.; Rogers, R. D.), Oxford University Press, New York, 2005;.
21. a) L. Liu, N. Zhao, O. A. Scherman, Chem. Commun. 2008, 1070-1072;
22. b) P. Montes-Navajas, A. Corma, H. Garcia, J. Mol. Catal. A 2008, 279, 165-169.
23. Gaussian 98 (Revision A.9), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
24. CCDC 722277 and 722278 contain the supplementary crystallography 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
25. R. Ahlrichs, M. Bär, M. Häser, H. Horn, C. Kölmel, Chem. Phys. Lett. 1989, 762, 165-169.
26. P.C. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213-222.
27. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
28. T. H. Dunning, Jr., J. Chem. Phys. 1989, 90, 1007-1023.
29. AMBER 9, D. A. Case, T.A. Darden, T.E. Cheatham III, C.L. Simmerling, J. Wang, R. E. Duke, R. Luo, K. M. Merz, D. A. Pearlman, M. Crowley, R. C. Walker, W. Zhang, B. Wang, S. Hayik, A. Roitberg, G. Seabra, K. F. Wong, F. Paesani, X. Wu, S. Brozell, V. Tsui, H. Gohlke, L. Yang, C. Tan, J. Mongan, V. Hornak, G. Cui, P. Beroza, D. H. Matthews, C. Schafmeister, W. S. Ross, P. A. Kollman, University of California, San Francisco, 2006.
30. J. Wang, R. M. Wolf, J. W. Caldwell, P. A. Kollman, D. A. Case, J. Comput. Chem. 2004, 25, 1157-1174.
31. W. L. Jorgensen, J. Chandrasekhar, J. Madura, M. L. Klein, J. Chem. Phys. 1983, 79, 926-935.
32. a) R. Marek, A. Lycka, Curr. Org. Chem. 2002, 6, 35-66;
33. b) R. Marek, A. Lycka, E. Kolehmainen, E. Sievanen, J. Tousek, Curr. Org. Chem. 2007, 11, 1154-1205.
34. R. Marek, L. Kralik, V. Sklenar, Tetrahedron Lett. 1997, 38, 665-668.
35. K. Moon, A. E. Kaifer, Org. Lett. 2004, 6, 185-188.