Bulletin of the Korean Chemical Society

  • 제32권1호
  • /
  • Pages.100-104
  • /
  • 2011
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

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

  • 투고 : 2010.09.07
  • 심사 : 2010.10.25
  • 발행 : 2011.01.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

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.

키워드

참고문헌

  1. Kumagai, H.; Hasegawa, M.; Miyanari, S.; Sugawa, Y.; Sato, Y.; Hori, T.; Ueda, S.; Kamiyama, H.; Miyano, S. Tetrahedron Lett. 1997, 38, 3971. https://doi.org/10.1016/S0040-4039(97)00792-2
  2. Shokova, E. A.; Kovalev, V. V. Russ. J. Org. Chem. 2003, 39, 1. https://doi.org/10.1023/A:1023416409935
  3. Lhotak, P. Eur. J. Org. Chem. 2004, 1675.
  4. Kim, T. H.; Lee, J. K.; Bok, J. H.; Kim, J. S.; Kim, H. Electrochim. Acta 2004, 49, 3759. https://doi.org/10.1016/j.electacta.2004.02.049
  5. Zlatuskova, P.; Stibor, I.; Tkadlecova, M.; Lhotak, P. Tetrahedron 2004, 60, 11383. https://doi.org/10.1016/j.tet.2004.09.088
  6. Appelhans, D.; Stastny, V.; Komber, H.; Voigt, D.; Lhotak, P.; Stibor, I. Tetrahedron Lett. 2004, 45, 7145. https://doi.org/10.1016/j.tetlet.2004.07.085
  7. Iki, N.; Kabuto, C.; Fukushima, T.; Kumagai, H.; Takeya, H.; Miyanari, S.; Miyashi, T.; Miyano, S. Tetrahedron 2000, 56, 1437. https://doi.org/10.1016/S0040-4020(00)00030-2
  8. Akdas, H.; Bringel, L.; Graf, E.; Hosseini, M. W.; Mislin, G.; Pansanel, J.; De Cian, A.; Fischer, J. Tetrahedron Lett. 1998, 39, 2311. https://doi.org/10.1016/S0040-4039(98)00067-7
  9. Bernardino, R. J.; Costa Cabral, B. J. J. Mol. Struct. (Theochem) 2001, 549, 253. https://doi.org/10.1016/S0166-1280(01)00521-8
  10. Matsumiya, H.; Terazono, Y.; Iki, N.; Miyano, S. J. Chem. Soc., Perkin Trans. 2 2002, 1166.
  11. Kim, K.; Choe, J.-I. J. Korean Chem. Soc. 2009, 53, 521. https://doi.org/10.5012/jkcs.2009.53.5.521
  12. Mandolini, L., Ungaro, R., Eds.; Calixarenes in Action; World Scientific Publishers Co.: Singapore, 2007.
  13. Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998.
  14. Calixarenes’ 50th Anniversary; Vicens, J., Asfari, Z., Harrowfield, J. M., Eds.; Kluwer: Dordrecht, 1995.
  15. Iki, N.; Miyano, S. J. Inclusion Phenom. Macro. Chem. 2001, 41, 99. https://doi.org/10.1023/A:1014406709512
  16. Lamartine, R.; Bavoux, C.; Vocanson, F.; Martin, A.; Senlis, G.; Perrin, M. Tetrahedron Lett. 2001, 42, 1021. https://doi.org/10.1016/S0040-4039(00)02131-6
  17. Bilyk, A.; Hall, A. K.; Harrowfield, J. M.; Hosseini, M. W.; Skelton, B. W.; White, A. H. Inorg. Chem. 2001, 40, 672. https://doi.org/10.1021/ic001008c
  18. Shokova, E. A.; Kovalev, V. V. Russ. J. Org. Chem. 2003, 39, 1. https://doi.org/10.1023/A:1023416409935
  19. Shokova, E. A.; Kovalev, V. V. Russ. Chem. Bull. 2003, 39, 13.
  20. Suwattanamala, A.; Magalhaes, A. L.; Gomes, J. A. N. F. Chem. Phys. Lett. 2004, 385, 368. https://doi.org/10.1016/j.cplett.2004.01.008
  21. Suwattanamala, A.; Magalhaes, A. L.; Gomes, J. A. N. F. J. Phys. Chem. A 2005, 109, 10742. https://doi.org/10.1021/jp054338x
  22. Iki, N.; Kumagai, H.; Morohashi, N.; Ejima, K.; Hasegawa, M.; Miyanari, S.; Miyano, S. Tetrahedron Lett. 1998, 39, 7559. https://doi.org/10.1016/S0040-4039(98)01645-1
  23. Mislin, G.; Graf, E.; Hosseini, M. W.; DeCian, A.; Fischer, J. Tetrahedron Lett. 1999, 40, 1129. https://doi.org/10.1016/S0040-4039(98)02586-6
  24. Mislin, G.; Graf, E.; Hosseini, M. W.; DeCian, A.; Fischer, J. Chem. Commun. 1998, 1345.
  25. Katagiri, H.; Hattori, T.; Morohashi, N.; Iki, N.; Miyano, S. J. Org. Chem. 2007, 72, 8327. https://doi.org/10.1021/jo701381h
  26. Lang, J.; Vlach, J.; Dvorakova, H.; Lhotak, P.; Himl, M.; Hrabal, R.; Stibor, I. J. Chem. Soc., Perkin Trans. 2 2001, 576.
  27. Morohashi, N.; Iki, N.; Sugawara, A.; Miyano, S. Tetrahedron 2001, 57, 5557. https://doi.org/10.1016/S0040-4020(01)00482-3
  28. Lhotak, P.; Svoboda, J.; Stibor, I.; Sykora, J. Tetrahedron Lett. 2002, 43, 7413. https://doi.org/10.1016/S0040-4039(02)01667-2
  29. HyperChem Release 7.5, Hypercube, Inc.: Waterloo, Ontario, Canada, 2002.
  30. Choe, J.-I.; Kim, K.; Chang, S.-K. Bull. Korean Chem. Soc. 2000, 21, 465. https://doi.org/10.1007/BF02705436
  31. Zhao, Y.; Tishchenko, O.; Truhlar, D. G. J. Phys. Chem. B 2005, 109, 19046. https://doi.org/10.1021/jp0534434
  32. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664. https://doi.org/10.1063/1.475428
  33. Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811. https://doi.org/10.1021/jp000497z
  34. 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.
  35. Private calculation by this author (Choe, J.-I.).
  36. Choe, J.-I. Bull. Korean Chem. Soc. 2010, 31, 3247. https://doi.org/10.5012/bkcs.2010.31.11.3247
  37. Lee, S. J.; Chung, H. Y.; Kim, K. S. Bull. Korean Chem. Soc. 2004, 25, 1061. https://doi.org/10.5012/bkcs.2004.25.7.1061

피인용 문헌

  1. vol.121, pp.37, 2017, https://doi.org/10.1021/acs.jpca.7b05733