Browse > Article
http://dx.doi.org/10.5012/bkcs.2008.29.10.1893

DFT Conformational Study of Calix[5]arene and Calix[4]arene: Hydrogen Bond  

Kim, Kwang-Ho (Department of Chemistry, Chung-Ang University)
Park, Seong-Jun (Department of Chemistry, Chung-Ang University)
Choe, Jong-In (Department of Chemistry, Chung-Ang University)
Publication Information
Bulletin of the Korean Chemical Society / v.29, no.10, 2008 , pp. 1893-1897 More about this Journal
Abstract
We have performed DFT calculations to investigate the conformational characteristics and hydrogen bonds of the p-tert-butylcalix[5]arene (1) and p-tert-butylcalix[4]arene (2). The structures of different conformers of 1 were optimized by using B3LYP/6-31+G(d,p) method. The relative stability of the various conformers of 1 is in the following order: cone (most stable) > 1,2-alternate > partial-cone > 1,3-alternate. The relative stability of four conformers of 2 is in the following order: cone (most stable) > partial-cone > 1,2-alternate > 1,3-alternate. The primary factor affecting the relative stabilities of the various conformers of the 1 and 2 are the number and strength of the intramolecular hydrogen bonds. The hydrogen-bond distances are discussed based on different calculation methods.
Keywords
DFT; B3LYP/6-31+G; Calix[5]arene; Calix[4]arene; Conformer; Hydrogen bond
Citations & Related Records
Times Cited By KSCI : 8  (Citation Analysis)
Times Cited By Web Of Science : 4  (Related Records In Web of Science)
Times Cited By SCOPUS : 5
연도 인용수 순위
1 Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998
2 Calixarenes 50th Anniversary: Commemorative Volume; Vicens, J.; Asfari, Z.; Harrowfield, J. M., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1991
3 Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989
4 Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1991
5 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
6 Pappalardo, S.; Parisi, M. F. J. Org. Chem. 1996, 61, 8724   DOI   ScienceOn
7 Arnaud-Neu, F.; Fuangswasdi, S.; Notti A.; Pappalardo, S.; Parisi, M. Angew. Chem. Int. Ed. 1998, 37, 112   DOI   ScienceOn
8 Giannetto, M.; Mori, G.; Notti, A.; Pappalardo, S.; Paris, M. F. Anal. Chem. 1998, 70, 4631   DOI   ScienceOn
9 Salvo, G. D.; Gattuso, G.; Notti, A.; Parisi, M.; Pappalardo, S. J. Org. Chem. 2002, 67, 684   DOI   ScienceOn
10 Gordon, J. L. M.; Böhmer, V.; Vogt, W. Tetrahedron Lett. 1995, 36, 2445   DOI   ScienceOn
11 Tan, L. V.; Quang, D. T.; Lee, M. H.; Kim, T. H.; Kim, H.; Kim, J. S. Bull. Korean Chem. Soc. 2007, 28, 791   DOI   ScienceOn
12 Coruzzi, M.; Andreetti, G. D.; Bocchi, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 1982, 2, 1133
13 Barrett, G.; McKervey, M. A.; Malone, J. F.; Walker, A.; Arnaud-Neu, F.; Guerra, L.; Schwing-Weill, M.-J. J. Chem. Soc. Perkin Trans. 2 1993, 1475
14 Stewart, D. R.; Krawiec, M.; Kashyap, R. P.; Watson, W. H.; Gutsche, C. D. J. Am. Chem. Soc. 1995, 117, 586   DOI   ScienceOn
15 Blixt, J.; Detellier, C. J. Am. Chem. Soc. 1995, 117, 8536   DOI
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 Gutsche, C. D.; Iqbal, M. Org. Syn. 1990, 68, 234   DOI
18 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
19 Choe, J.-I.; Lee, S. H.; Oh, D.-S.; Chang, S.-K.; Nanbu, S. Bull. Korean Chem. Soc. 2004, 25, 190   DOI   ScienceOn
20 Harada, T.; Rudzinski, J. M.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1992, 2, 2109
21 Harada, T.; Rudzinski, J. M.; Shinkai, S. Tetrahedron 1993, 49, 5941   DOI   ScienceOn
22 Souley, B.; Asfari, Z.; Vicens, J. Polish J. Chem. 1993, 67, 763
23 Gutsche, C. D. Top. Curr. Chem. 1984, 123, 1   DOI
24 Gutsche, C. D. Acc. Chem. Res. 1983, 16, 161   DOI
25 Andreetti, G. D.; Ungaro, R.; Pochini, A. J. Chem. Soc., Chem. Comm. 1979, 1005
26 Cambridge Structure Database; Cambridge Crystallographic Data Centre: Cambridge, U. K., 2008
27 Bernardino, R. J.; Costa Cabral, B. J. J. Phys. Chem. A 1999, 103, 9080   DOI   ScienceOn
28 Bernardino, R. J.; Costa Cabral, B. J.; Pereira, J. L. C. J. Mol. Struc. (THEOCHEM) 1998, 23, 455
29 Pak, C.: Lee, H. M.; Kim, J. C.; Kim, D.; Kim, K. S. Struct. Chem. 2005, 16, 187   DOI   ScienceOn
30 Atwood, J. L.; Barbour, L. J.; Heaven, M. W.; Raston, C. L. Angew. Chem. 2003, 42, 3254   DOI   ScienceOn
31 Clark, T. E.; Makha, M.; Raston, C. L.; Sobolev, A. N. Cryst. Growth Des. 2006, 6, 2783   DOI   ScienceOn
32 HyperChem Release 7.5; Hypercube, Inc.: Waterloo, Ontario, Canada, 2002
33 Choe, J.-I.; Kim, K.; Chang, S.-K. Bull. Korean Chem. Soc. 2000, 21, 465   DOI   ScienceOn
34 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.11.3; Gaussian, Inc.: Pittsburgh, PA, 1998
35 Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford Univ. Press: Cambridge, 1997
36 Keller, S. W.; Schuster, G. M.; Tobiason, F. L. Polym. Mater. Sci. Eng. 1987, 57, 906
37 Chem3D, Version 7.0; Cambridge Soft: Cambridge, MA, U.S.A., 2001
38 Agnihotri, P.; Suresh, E.; Paul, P.; Ghosh, P. K. Eur. J. Inorg. Chem. 2006, 3369
39 Lee, S. J.; Chung, H. Y.; Kim, K. S. Bull. Korean Chem. Soc. 2004, 25, 1061   DOI   ScienceOn
40 Jeon, Y.-M.; Lim, T.-H.; Kim, J.-G.; Kim, J.-S.; Gong, M.-S. Bull. Korean Chem. Soc. 2007, 28, 816   DOI   ScienceOn
41 Fukazawa, Y.; Yoshimura, K.; Sasaki, S.; Yamazaki, M.; Okajima, T. Tetrahedron 1996, 52, 2301   DOI   ScienceOn
42 Riehn, C.; Reimann, B.; Buchhold, K.; Barth, H.-D.; Vaupel, S.; Brutschy, B.; Tarakeshwar, P.; Kim, K. S. J. Chem. Phys. 2001, 115, 10045   DOI   ScienceOn
43 Choe, J.-I.; Lee, S. H.; Oh, D.-S. Bull. Korean Chem. Soc. 2004, 25, 55   DOI   ScienceOn
44 Choe, J.-I.; Chang, S.-K. Bull. Korean Chem. Soc. 2002, 23, 48   DOI   ScienceOn
45 Choe, J.-I.; Chang, S.-K.; Satoshi, M.; Nanbu, S. Bull. Korean Chem. Soc. 2003, 24, 75   DOI   ScienceOn
46 Choe, J.-I.; Lee, S. H. Bull. Korean Chem. Soc. 2004, 25, 553   DOI   ScienceOn
47 Brouwer, E. B.; Udachin, K. A.; Enright, G. D.; Ripmeester, J. A. Chem.Commun. 2000, 1905
48 Ninagawa, A.; Matsuda, H. Makromol. Chem. Rapid Commun. 1982, 3, 65   DOI
49 Clark, T. J. Mol. Struc. (Theochem) 2000, 530, 1   DOI   ScienceOn
50 Souley, B.; Asfari, Z.; Vicens, J. Polish J. Chem. 1992, 66, 959
51 Kamerer, H.; Happel, G.; Mathiasch, B. Makromol. Chem. 1981, 182, 1685   DOI
52 Calixarenes in Action; Mandolini, L.; Ungaro, R., Eds.; World Scientific Publishers Co.: Singapore, 2007
53 Markowitz, M. A.; Janout, V.; Castner, D. G.; Regen, S. L. J. Am. Chem. Soc. 1989, 111, 8192   DOI
54 van Hoorn, W. P.; Briels, W. J.; van Duynthoven, J. P. M.; van Veggel, F. C. J. M.; Reinhoudt, D. N. J. Org. Chem. 1998, 63, 1299   DOI   ScienceOn
55 Harada, T.; Ohseto, F.; Shinkai, S. Tetrahedron 1994, 50, 13377   DOI   ScienceOn
56 van Hoorn, W. P.; Morshuis, M. G. H.; van Veggel, F. C. J. M.; Reinhoudt, D. N. J. Phys. Chem. 1998, 102, 1130   DOI   ScienceOn