Browse > Article
http://dx.doi.org/10.5012/bkcs.2009.30.3.589

DFT Study of p-tert-Butylcalix[6]aryl Ester Complexed with Alkylammonium Ions  

Kim, Kwang-Ho (Department of Chemistry, Chung-Ang University)
Choe, Jong-In (Department of Chemistry, Chung-Ang University)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.3, 2009 , pp. 589-594 More about this Journal
Abstract
We have performed DFT B3LYP/6-31G(d,p) calculations to investigate the complexation behaviors of the ethyl ester derivative of p-tert-butylcalix[6]arene (1) toward a variety of alkylammonium ions. We have studied the binding sites of these host-guest complexes focusing on the p-tert-butylcalix[6]arene pocket (endo) of 1. The smaller alkylammonium cations have the better complexation efficiency than the bulkier alkylammonium ions with the p-tert-butylcalix[6]aryl ester. The hydrogen-bonding of N-H$\ldots$O is one of the important factors for the complexation behavior of the p-tert-butylcalix[6]aryl ester, in addition to the NH-aromatic π, CH-aromatic π and electrostatic interactions, and the steric hindrance of alkylammonium cation. The hydrogen-bonded distances and angles of N-H$\ldots$O are reported for the complexes of the p-tert-butylcalix[6]aryl ester with various alkylammonium ions.
Keywords
DFT, B3LYP/6-31G(d,p); Calix[6]aryl ester; Alkylammonium ions; Hydrogen bond;
Citations & Related Records
Times Cited By KSCI : 5  (Citation Analysis)
Times Cited By Web Of Science : 0  (Related Records In Web of Science)
Times Cited By SCOPUS : 0
연도 인용수 순위
1 Inclusion Phenomena and Molecular Recognition; Atwood, J. L., Ed.; Plenum Press: New York, 1989.
2 Balzani, V.; De Cola, L. Supramolecular Chemistry; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992   DOI   ScienceOn
3 Bauer, L. J.; Gutsche, C. D. J. Am. Chem. Soc. 1985, 107, 6063   DOI   ScienceOn
4 Choe, J.-I.; Kim, K.; Chang, S.-K. Bull. Korean Chem. Soc. 2000, 21, 200   DOI   ScienceOn
5 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
6 Oh, D.-S.; Choe, J.-I. Bull. Korean Chem. Soc. 2007, 28, 596   DOI   ScienceOn
7 Computational Approaches in Supramolecular Chemistry; Wipff, G., Ed.; Kluwar Academic Publishers: Dordrecht, The Netherlands, 1994   DOI   ScienceOn
8 Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785   DOI   ScienceOn
9 Su, C. C.; Lu, L. H.; Liu, L. K. J. Phys. Chem. A 2003, 107, 4563   DOI   ScienceOn
10 Hsieh, T. J.; Su, C. C.; Chen, C. Y.; Liou, C. H.; Lu, L. H. J. Mol. Struct. 2005, 741, 193   DOI   ScienceOn
11 Fages, F.; 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
12 Rogers, J. S.; Gutsche, C. D. J. Org. Chem. 1992, 57, 3152.   DOI
13 Gutsche, C. D.; See, K. A. J. Org. Chem. 1992, 57, 4527   DOI
14 Shinkai, S. Tetrahedron 1993, 40, 8933
15 Shinkai, S.; Koreishi, H.; Ueda, K.; Arimura, T.; Manabe, O. J. Am. Chem. Soc. 1987, 109, 6371   DOI
16 Chang, S.-K.; Hwang, H.-S.; Son, H.; Youk, J.; Kang, Y. S. J. Chem. Soc., Chem. Commun. 1991, 217   DOI
17 Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: Cambridge, 1997
18 Salvo, G. D.; Gattuso, G.; Notti, A.; Parisi, M.; Pappalardo, S. J. Org. Chem. 2002, 67, 684   DOI   ScienceOn
19 Lee, S. J.; Chung, H. Y.; Kim, K. S. Bull. Korean Chem. Soc. 2004, 25, 1061   DOI   ScienceOn
20 Chem3D, Version 7.0; Cambridge Soft, Cambridge, MA, U.S.A., 2001
21 Cho, S. J.; Hwang, H.; Park, J.; Oh, K. S.; Kim, K. S. J. Am. Chem. Soc. 1996, 118, 485   DOI   ScienceOn
22 Choe, J.-I.; Lee, S. H.; Oh, D.-S.; Chang, S.-K.; Nanbu, S. Bull. Korean Chem. Soc. 2004, 25, 190   DOI   ScienceOn
23 Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J. W. Chem. Lett. 1995, 4, 297
24 Ahn, S.; Mun, C. S.; Chung, K. S.; Oh, W. S.; Chang, S.-K.; Lee, J. W. Bull. Korean Chem. Soc. 1998, 19, 68   DOI   ScienceOn
25 HyperChem Release 7.5; Hypercube, Inc.: Waterloo, Ontario, Canada, 2002
26 Hohenberg, P.; Kohn, W. Phys. Rev. B 1964, 136, 785
27 Karr, P. A.; Zandler, M. E.; Beck, M.; Jaeger, J. D.; McCarty, A. L.; Smith, P. M.; D'Souza, F. J. Mol. Struct. (Theochem.) 2006, 765, 91   DOI   ScienceOn
28 Kohn, W.; Sham, L. J. Phys. Rev. A 1965, 140, 1133   DOI
29 Sreeruttun, R. K.; Ramasami, P.; Yan, G.; Wannere, C. S.; Schleyer, P. v. R.; Schaefer, H. F. Int. J. Mass Spectrom. 2005, 241, 295   DOI   ScienceOn
30 Zandler, M. E.; D'Souza, F. C. R. Chimie. 2006, 9, 960
31 Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; 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.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision D.01; Gaussian, Inc: Wallingford, CT, 2004
32 Casnati, A.; Minari, P.; Pochini, A.; Ungaro, R. J. Chem. Soc., Chem. Commun. 1991, 1413.
33 Choe, H. S.; Kim, D.; Tarakeshwar, P.; Suh, S. B.; Kim, K. S. J. Org. Chem. 2002, 67, 1848   DOI   ScienceOn
34 Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J.; Bohmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1991.
35 Behr, J.-P.; Lehn, J.-M.; Vierling, P. Helv. Chim. Acta 1982, 65, 1853.   DOI
36 Bradshaw, J. S.; Baxter, S. L.; Lamb, J. D.; Izatt, R. M.; Christensen, J. J. J. Am. Chem. Soc. 1981, 103, 1821.   DOI
37 Kanamathareddy, S.; Gutsche, C. D. J. Org. Chem. 1992, 57, 3160.   DOI
38 Neri, P.; Pappalardo, S. J. Org. Chem. 1993, 58, 1048.   DOI   ScienceOn
39 Calixarenes 50th Anniversary: Commemorative Volume; Vicens, J.; Asfari, Z.; Harrowfield, J. M., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1991.   DOI   ScienceOn
40 Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998.
41 Choi, H. S.; Cho, S. J.; Kim, K. S. Proc. Natl. Acad. Sci. 1998, 95, 12094.   DOI
42 Kim, K. S.; Cui, C.; Cho, S. J. J. Phys. Chem. 1998, 102, 461.   DOI   ScienceOn
43 Lee, J. H.; Kim, T. H.; Chang, S.-K.; Choe, J.-I. Supramolecular Chemistry 1995, 4, 315.   DOI
44 Kim, K. S.; Lee, J. Y.; Lee, S. J.; Ha, T. K.; Kim, D. H. J. Am. Chem. Soc. 1994, 116, 7399.   DOI   ScienceOn
45 Han, S. Y.; Kang, M.-H.; Jung, Y. E.; Chang, S.-K. J. Chem. Soc., Perkin Trans. 2 1994, 835.
46 Calixarenes in Action; Mandolini, L.; Ungaro, R., Eds.; World Scientific Publishers Co.: Singapore, 2007.
47 Chang, S.-K.; Jang, M.; Han, S. Y.; Lee, J. H.; Kang, M. H.; No, K. T. Chem. Lett. 1992, 1937.