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http://dx.doi.org/10.5012/bkcs.2002.23.6.891

Ab Initio Study of Conformers of p-tert-Butylcalix[4]crown-6-ether Complexed with Alkyl Ammonium Cations  

Choe, Jong-In
Jang, Suk-Kyu
Nanbu, Shinkoh
Publication Information
Bulletin of the Korean Chemical Society / v.23, no.6, 2002 , pp. 891-896 More about this Journal
Abstract
The structures and energies of p-tert-butylcalix[4]crown-6-ether(1) in various conformers and their alkyl ammonium complexes have been calculated by ab initio HF/6-31G quantum mechanics method. We have tried to obtain the relative affinity of partial-cone and 1,3-alternate conformers of 1 for alkyl ammonium guests by comparison with its cone-shaped analogue. We have also calculated the relative complexation efficiency of these host-guest complexes focusing on the binding sites of $crown-\sigma-enther$ moiety or benzene-rings pocket of the host molecule 1. These calculations revealed that the crown moiey has better complexation efficiency than upper rim part of calyx[4]arene that is in similar trend to the cone-shaped complexes.
Keywords
Calix[4]crown-6-ether; Partial cone; 1,3-Alternate; Alkyl ammonium ions; Molecular recognition;
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1 Lee, J. Y; Lee, S. J.; Choi, H. S.; Cho, S. J.; Kim, K. S.; Ha, T. K. Chem. Phys. lett. 1995, 232, 67.   DOI   ScienceOn
2 Kubo, Y; Maeda, S.; Tokita, S.; Kubo, M. Nature 1996, 382, 522.   DOI   ScienceOn
3 Computational Approaches in Supramolecular Chemistry; Wipff, G., Ed.; Kluwar Academic Publishers: Dordrecht, The Netherlands, 1994.
4 Calixarenes: A Versatile Class of Macro-cyclic Compounds; Vicens, J., Bohmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1991.
5 Reetz, M. T; Niemeyer, C. M; Harms, K. Angew. Chem. Int. Ed. Engl. 1991, 30, 1474.   DOI
6 Baaden, M.; Berny, E; Muzet, N; Troxler, L.; Wipff, G. In Calixarenes for Separations; Lumetta, G. J., Rogers, R. D., Gopalan, A. S., Eds.; ACS Symposium Series 757; ACS: Washington, DC, 2000; Chap. 6.
7 Choe, J.-L; Chang, S.-K.; Ham, S. W.; Nanbu, S.; Aoyagi, M. Bull. Korean Chem. Soc. 2001, 22, 1248.
8 Burkert, U.; Allinger, N. L. Molecular Mechanics; ACS Monograph 177, American Chemical Society, Washington, D.C. 1982.
9 Behr, J.-P; Lehn, J.-M.; Vierling, P. Helv. Chim. Acta 1982, 65, 1853.   DOI
10 Cation Binding by Macrocycles; Inoue, Y, Gokel, G. W., Eds.; Marcel Dekker; New York, 1990.
11 Allinger, N. L.; Yuh, Y H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551.   DOI
12 Jung, Y E.; Song, B. M.; Chang, S.-K. J. Chem. Soc, Perkin Trans. 2 1995, 2031.
13 Bradshaw, J. S.; Baxter, S. L.; Lamb, J. D.; Izatt, R. M; Christensen, J. J. J. Am. Chem. Soc. 1981, 103, 1821.   DOI
14 Chang, S.-K.; Hwang, H.-S.; Son, H.; Youk, J.; Kang, Y. S. J. Chem. Soc, Chem. Commun. 1991, 217.
15 Choi, H. S.; Cho, S. J.; Kim, K. S. Proc. Natl. Acad. Sci. 1998, 95, 12094.   DOI
16 Hwang, S.; Jang, Y H.; Ryu, G. H.; Chung, D. S. Bull. Korean Chem. Soc. 1999,10, 1129.
17 Fages, E; Desvergne, J.-P; Kampke, K.; Bouas-Laurent, H.; Lehn, J.-M.; Meyer, M.; Albrecht-Gary, A.-M. J. Am. Chem. Soc. 1993,115, 3658.   DOI   ScienceOn
18 HyperChem Release 6.03; Hypercube, Inc.: Waterloo, Ontario, Canada, 2001.
19 Czech, A.; Czech, B. P.; Bartsch, R. A.; Chang, C. A.; Ochaya, V. O. J. Org. Chem. 1988, 53, 5.   DOI
20 Kim, K. S.; Cui, C; Cho, S. J. J. Phys. Chem. 1998, 102, 461.   ScienceOn
21 Cho, S. J.; Hwang, H.; Park, J.; Oh, K.S.; Kim, K. S. J. Am. Chem. Soc. 1996,118, 485.   DOI   ScienceOn
22 Kim, K. S.; Lee, J. Y; Lee, S. J.; Ha, T. K.; Kim, D. H. J. Am. Chem. Soc. 1994,116, 7399.   DOI
23 Discover User's Guide, Versions 2.9/3.1.0; Biosym Technologies (presently merged to MSI): San Diego, 1993.
24 Choe, J.-L; Kim, K.; Chang, S.-K. Bull. Korean Chem. Soc. 2000, 21, 465.   DOI
25 Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989.
26 Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. Jr.; Stratmann, R. E.; Burant, J. C; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N; Strain, M. C; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C; Adamo, C; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.