Browse > Article
http://dx.doi.org/10.5012/bkcs.2004.25.4.553

Ab Initio Study of the Conformational Isomers of Tetraethyl and Triethyl Esters of Calix[4]arene  

Choe, Jong-In (Department of Chemistry, Chung-Ang University)
Lee, Sang-Hyun (Department of Chemistry, Chung-Ang University)
Publication Information
Bulletin of the Korean Chemical Society / v.25, no.4, 2004 , pp. 553-556 More about this Journal
Abstract
In this study we have performed ab initio computer simulations to investigate the conformational characteristics of the tetraethyl (1) and triethyl ester (2) of p-tert-butylcalix[4]arene. The structures of different conformational isomers for each compound have been optimized using ab initio RHF/6-31G methods. After optimization, B3LYP/6-31+G(d,p) single point calculations of the final structures are done to include the effect of electron correlation and the basis set with diffuse function and polarization function. Relative stability of tetraethyl ester (1) of p-tert-butylcalix[4]arene is in following order: cone (most stable) > partial cone > 1,3- alternate > 1,2-alternate isomer. Relative stability of triethyl ester (2) of p-tert-butylcalix[4]arene is in following order: cone (most stable) > 2-partial cone > 1-partial cone > 3-partial cone ~ 1,3-alternate ~ 1,2- alternate isomer.
Keywords
Ab initio calculation; HF/6-31G; Calix[4]arene esters; Conformational isomer; Cone;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By Web Of Science : 7  (Related Records In Web of Science)
Times Cited By SCOPUS : 7
연도 인용수 순위
1 Minamino, S.; Choe, J.-I.; Chang, S.-K.; Mizutani, F.; Nanbu, S.Chem. Phys. Lett. 2003, 374, 572.   DOI   ScienceOn
2 Gutsche, C. D.; Bauer, L. J. Tetrahedron Lett. 1981, 22, 4763.   DOI   ScienceOn
3 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
4 HyperChem Release 6.3; Hypercube, Inc.: Waterloo, Ontario,Canada, 2001.
5 Choe, J.-I.; Kim, K.; Chang, S.-K. Bull. Korean Chem. Soc.2000, 21, 465.   DOI
6 Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989.
7 Hong, B. H.; Bae, S. C.; Lee, C.-W.; Jeong,S.; Kim, K. S. Science 2001, 294, 348.   DOI   ScienceOn
8 Kim, K. S. Curr. Appl. Phys. 2002, 2, 65.   DOI   ScienceOn
9 Choe, J.-I.; Chang, S.-K.; Nanbu, S. Bull. Korean Chem. Soc. 2002, 23,891.   DOI   ScienceOn
10 Balzani, V.; De Cola, L. Supramolecular Chemistry;Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992.
11 Harada, T.; Rudzinski, J. M.; Shinkai, S. Tetrahedron 1993, 49, 5941.   DOI   ScienceOn
12 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.   DOI   ScienceOn
13 Harada, T.; Rudzinski, J. M.; Shinkai, S. J. Chem. Soc., PerkinTrans. 1992, 2, 2109.
14 Harada, T.; Ohseto, F.; Shinkai, S.Tetrahedron 1994, 50, 13377.   DOI   ScienceOn
15 Choe, J.-I.; Chang, S.-K.; Ham, S. W.; Nanbu,S.; Aoyagi, M. Bull. Korean Chem. Soc. 2001, 22, 1248.
16 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
17 Choe, J.-I.; Lee, S. H.; Oh, D.-S. Bull. Korean Chem. Soc. 2004,25, 55.   DOI   ScienceOn
18 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
19 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
20 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
21 Computational Approaches in Supramolecular Chemistry; Wipff,G., Ed.; Kluwar Academic Publishers: Dordrecht, The Netherlands,1994.
22 Calixarenes: A Versatile Class of MacrocyclicCompounds; Vicens, J., Böhmer, V., Eds.; Kluwer AcademicPublishers: Dordrecht, The Netherlands, 1991.
23 Wipff, G.; Guilbaud, P.; Varnek, A. J. Am. Chem. Soc. 1993, 115,8298.   DOI   ScienceOn
24 Kim, K. S. Bull. Korean Chem. Soc. 2003, 24, 757.   DOI