Browse > Article
http://dx.doi.org/10.5012/bkcs.2011.32.1.100

mPW1PW91 Conformational Study of Di-t-butyl-dinitro-tetramethoxysulfonylcalix[4]arene  

Choe, Jong-In (Department of Chemistry, Chung-Ang University)
Publication Information
Abstract
The structures of the conformers for 1,3-di-t-butyl-2,4-dinitro-tetramethoxysulfonylcalix[4]arene (1) and 1,2-di-t-butyl-3,4-dinitro-tetramethoxysulfonylcalix[4]arene (2) were optimized using DFT BLYP and mPW1PW91/6-31G(d,p) (hybrid HF-DF) calculation methods. We have analyzed the total electronic and Gibbs free energies and the differences between the various conformations (cone, partial-cone (PC), 1,2-alternate, and 1,3-alternate) of 1 and 2. For both compounds, the 1,3-alternate (1,3-A) conformers were calculated to be the most stable, which correlate very well with the experimental results. The orderings of the relative stability of 1 and 2 that resulted from the mPW1PW91/6-31G(d,p) calculations are the following: 1: 1,3-A (syn) > PC (syn) > PC (anti) > 1,2-A (anti) > CONE (syn); 2: 1,3-A (anti) > PC (anti) > PC (syn) > 1,2-A (anti) > 1,2-A (syn) > CONE (syn). The BLYP/6-31G(d) calculated IR spectra of the most stable 1,3-A conformers of 1 and 2 are compared.
Keywords
mPW1PW91; BLYP; Conformer; 1,3-Alternate; Thiacalix[4]arene;
Citations & Related Records
Times Cited By KSCI : 3  (Citation Analysis)
Times Cited By Web Of Science : 0  (Related Records In Web of Science)
Times Cited By SCOPUS : 0
연도 인용수 순위
1 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.
2 Private calculation by this author (Choe, J.-I.).
3 Choe, J.-I. Bull. Korean Chem. Soc. 2010, 31, 3247.   DOI   ScienceOn
4 Lee, S. J.; Chung, H. Y.; Kim, K. S. Bull. Korean Chem. Soc. 2004, 25, 1061.   DOI   ScienceOn
5 Mislin, G.; Graf, E.; Hosseini, M. W.; DeCian, A.; Fischer, J. Tetrahedron Lett. 1999, 40, 1129.   DOI   ScienceOn
6 Mislin, G.; Graf, E.; Hosseini, M. W.; DeCian, A.; Fischer, J. Chem. Commun. 1998, 1345.
7 Katagiri, H.; Hattori, T.; Morohashi, N.; Iki, N.; Miyano, S. J. Org. Chem. 2007, 72, 8327.   DOI   ScienceOn
8 Lang, J.; Vlach, J.; Dvorakova, H.; Lhotak, P.; Himl, M.; Hrabal, R.; Stibor, I. J. Chem. Soc., Perkin Trans. 2 2001, 576.
9 Morohashi, N.; Iki, N.; Sugawara, A.; Miyano, S. Tetrahedron 2001, 57, 5557.   DOI   ScienceOn
10 Choe, J.-I.; Kim, K.; Chang, S.-K. Bull. Korean Chem. Soc. 2000, 21, 465.   DOI
11 Lhotak, P.; Svoboda, J.; Stibor, I.; Sykora, J. Tetrahedron Lett. 2002, 43, 7413.   DOI   ScienceOn
12 HyperChem Release 7.5, Hypercube, Inc.: Waterloo, Ontario, Canada, 2002.
13 Zhao, Y.; Tishchenko, O.; Truhlar, D. G. J. Phys. Chem. B 2005, 109, 19046.   DOI
14 Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664.   DOI   ScienceOn
15 Matsumiya, H.; Terazono, Y.; Iki, N.; Miyano, S. J. Chem. Soc., Perkin Trans. 2 2002, 1166.
16 Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811.   DOI   ScienceOn
17 Akdas, H.; Bringel, L.; Graf, E.; Hosseini, M. W.; Mislin, G.; Pansanel, J.; De Cian, A.; Fischer, J. Tetrahedron Lett. 1998, 39, 2311.   DOI   ScienceOn
18 Bernardino, R. J.; Costa Cabral, B. J. J. Mol. Struct. (Theochem) 2001, 549, 253.   DOI   ScienceOn
19 Kim, K.; Choe, J.-I. J. Korean Chem. Soc. 2009, 53, 521.   DOI   ScienceOn
20 Mandolini, L., Ungaro, R., Eds.; Calixarenes in Action; World Scientific Publishers Co.: Singapore, 2007.
21 Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998.
22 Calixarenes’ 50th Anniversary; Vicens, J., Asfari, Z., Harrowfield, J. M., Eds.; Kluwer: Dordrecht, 1995.
23 Iki, N.; Miyano, S. J. Inclusion Phenom. Macro. Chem. 2001, 41, 99.   DOI
24 Lamartine, R.; Bavoux, C.; Vocanson, F.; Martin, A.; Senlis, G.; Perrin, M. Tetrahedron Lett. 2001, 42, 1021.   DOI   ScienceOn
25 Bilyk, A.; Hall, A. K.; Harrowfield, J. M.; Hosseini, M. W.; Skelton, B. W.; White, A. H. Inorg. Chem. 2001, 40, 672.   DOI   ScienceOn
26 Shokova, E. A.; Kovalev, V. V. Russ. J. Org. Chem. 2003, 39, 1.   DOI
27 Shokova, E. A.; Kovalev, V. V. Russ. Chem. Bull. 2003, 39, 13.
28 Suwattanamala, A.; Magalhaes, A. L.; Gomes, J. A. N. F. Chem. Phys. Lett. 2004, 385, 368.   DOI   ScienceOn
29 Iki, N.; Kumagai, H.; Morohashi, N.; Ejima, K.; Hasegawa, M.; Miyanari, S.; Miyano, S. Tetrahedron Lett. 1998, 39, 7559.   DOI   ScienceOn
30 Suwattanamala, A.; Magalhaes, A. L.; Gomes, J. A. N. F. J. Phys. Chem. A 2005, 109, 10742.   DOI   ScienceOn
31 Kumagai, H.; Hasegawa, M.; Miyanari, S.; Sugawa, Y.; Sato, Y.; Hori, T.; Ueda, S.; Kamiyama, H.; Miyano, S. Tetrahedron Lett. 1997, 38, 3971.   DOI   ScienceOn
32 Shokova, E. A.; Kovalev, V. V. Russ. J. Org. Chem. 2003, 39, 1.   DOI
33 Lhotak, P. Eur. J. Org. Chem. 2004, 1675.
34 Kim, T. H.; Lee, J. K.; Bok, J. H.; Kim, J. S.; Kim, H. Electrochim. Acta 2004, 49, 3759.   DOI   ScienceOn
35 Zlatuskova, P.; Stibor, I.; Tkadlecova, M.; Lhotak, P. Tetrahedron 2004, 60, 11383.   DOI   ScienceOn
36 Appelhans, D.; Stastny, V.; Komber, H.; Voigt, D.; Lhotak, P.; Stibor, I. Tetrahedron Lett. 2004, 45, 7145.   DOI   ScienceOn
37 Iki, N.; Kabuto, C.; Fukushima, T.; Kumagai, H.; Takeya, H.; Miyanari, S.; Miyashi, T.; Miyano, S. Tetrahedron 2000, 56, 1437.   DOI   ScienceOn