Browse > Article
http://dx.doi.org/10.5012/bkcs.2004.25.1.055

Ab Initio Study of the Conformations of Tetramethoxycalix[4]arenes  

Choe, Jong-In (Department of Chemistry, Chung-Ang University)
Lee, Sang-Hyun (Department of Chemistry, Chung-Ang University)
Oh, Dong-Suk (Department of Chemistry, Chung-Ang University)
Publication Information
Bulletin of the Korean Chemical Society / v.25, no.1, 2004 , pp. 55-58 More about this Journal
Abstract
In this study we have performed ab initio computer simulations to investigate the conformational characteristics of the tetramethoxycalix[4]arenes (1 and 2). The structures of four types (cone, partial cone, 1,2-alternate, and 1,3-alternate) of conformers for each compound have been optimized using ab initio RHF/6-31G and 6-31$G^{**}$ methods. General trends in relative stabilities of tetramethyl ether derivatives of calix[4]arene 1 and p-tert-butylcalix[4]arene 2 are similar and decrease in following order: partial cone (most stable) > cone > 1,3-alternate > 1,2-alternate. The calculated results of the most stable conformation of partial cone structure agree with the reported NMR experimental observations.
Keywords
Ab initio calculation; RHF/6-31$G^{**}$; Calix[4]arene; Conformations; Partial cone;
Citations & Related Records

Times Cited By Web Of Science : 8  (Related Records In Web of Science)
Times Cited By SCOPUS : 9
연도 인용수 순위
1 Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989.
2 Grootenhuis, P. D. J.; Kollman, P. A.; Groenen, L. C.; Reinhoudt,D. N.; van Hummel, G. J.; Ugozzoli, F.; Andreetti, G. D. J. Am.Chem. Soc. 1990, 112, 4165.   DOI
3 MM3: Molecular Mechanics 3; Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551.   DOI
4 Kim, K. S. Curr. Appl. Phys. 2002, 2, 65.   DOI   ScienceOn
5 Balzani, V.; De Cola, L. Supramolecular Chemistry; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992.
6 Harada, T.; Rudzinski, J. M.; Shinkai, S. Tetrahedron 1993, 49, 5941.   DOI   ScienceOn
7 Suh, S. B.; Hong, B. H.; Tarakeshwar, P.; Youn, S. J.; Jeong, S. ; Kim, K. S. Phys. Rev. B 2003, 67, 241402(R).   DOI   ScienceOn
8 HyperChem Release 6.3; Hypercube, Inc.: Waterloo, Ontario, Canada, 2001.
9 Gutsche, C. D.; Bauer, L. J. Tetrahedron Lett. 1981, 22, 4763.   DOI   ScienceOn
10 van Hoorn, W. P.; Briels, W. J.; van Duynthoven, J. P. M.; vanVeggel, F. C. J. M.; Reinhoudt, D. N. J. Org. Chem. 1998, 63,1299.   DOI   ScienceOn
11 Kim, K. S. Bull. Korean Chem. Soc. 2003, 24, 757.   DOI
12 Burkert, U.; Allinger, N. L. Molecular Mechanics; ACS Monograph 177, American Chemical Society: Washington, D.C. 1982.
13 Choe, J.-I.; Chang, S.-K.; Ham, S. W.; Nanbu, S.; Aoyagi, M. Bull. Korean Chem. Soc. 2001, 22, 1248.
14 Calixarenes: A Versatile Class of MacrocyclicCompounds; Vicens, J., Bohmer, V., Eds.; Kluwer AcademicPublishers: Dordrecht, The Netherlands, 1991.
15 Choe, J.-I.; Chang, S.-K.; Nanbu, S. Bull. Korean Chem. Soc. 2002, 23, 891.
16 Hong, B. H.; Bae, S. C.; Lee, C.-W.; Jeong, S.; Kim, K. S. Science 2001, 294, 348.   DOI   ScienceOn
17 Harada, T.; Ohseto, F.; Shinkai, S. Tetrahedron 1994, 50, 13377.   DOI   ScienceOn
18 Choe, J.-I.; Kim, K.; Chang, S.-K. Bull. Korean Chem. Soc. 2000, 21, 465.   DOI
19 Hong, B. H.; Lee, J. Y.; Lee, C.-W.; Kim, J. C.; Bae, S. C.; Kim, K. S. J. Am. Chem. Soc. 2001, 123, 10748.
20 Wipff, G.; Guilbaud, P.; Varnek, A. J. Am. Chem. Soc. 1993, 115,8298.   DOI   ScienceOn
21 Harada, T.; Rudzinski, J. M.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1992, 2, 2109.
22 Fisher, S.; Grootenhuis, P. D. J.; Groonen, L. C.; van Hoorn, W. P.; van Veggel, F. C. J. M.; Reinhoudt, D. N.; Karplus, M. J. Am. Chem. Soc. 1996, 117, 1610.
23 Computational Approaches in Supramolecular Chemistry; Wipff, G., Ed.; Kluwar Academic Publishers: Dordrecht, The Netherlands, 1994.
24 Groonen, L. C.; van Loon, J.-D.; Verboom, W.; Harkema, S.;Casnati, A.; Ungaro, R.; Pochini, A.; Ugozzoli, F.; Reinhoudt, D.N. J. Am. Chem. Soc. 1991, 113, 2385.   DOI
25 Kim, K. S.;Suh, S. B.; Kim, J. C.; Hong, B. H.; Lee, E. C.; Yun, S.; Tarakeshwar, P.; Lee, J. Y.; Kim, Y.; Ihm, H.; Kim, H. G.; Lee, J. W.; Kim, J. K.; Lee, H. M.; Kim, D.; Cui, C.; Youn, S. J.; Chung, H. Y.; Choi, H. S.; Lee, C.-W.; Cho, S. J.; Jeong, S.; Cho, J.-H. J. Am. Chem. Soc. 2002, 124, 14268.   DOI   ScienceOn
26 Inclusion Phenomena and Molecular Recognition; Atwood, J. L., Ed.; Plenum Press: New York, 1989.