Bulletin of the Korean Chemical Society

  • 제25권4호
  • /
  • Pages.553-556
  • /
  • 2004
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

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

  • 발행 : 2004.04.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

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.

키워드

참고문헌

  1. Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989.
  2. Calixarenes: A Versatile Class of MacrocyclicCompounds; Vicens, J., Böhmer, V., Eds.; Kluwer AcademicPublishers: Dordrecht, The Netherlands, 1991.
  3. Computational Approaches in Supramolecular Chemistry; Wipff,G., Ed.; Kluwar Academic Publishers: Dordrecht, The Netherlands,1994.
  4. Balzani, V.; De Cola, L. Supramolecular Chemistry;Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992.
  5. Wipff, G.; Guilbaud, P.; Varnek, A. J. Am. Chem. Soc. 1993, 115,8298. https://doi.org/10.1021/ja00071a044
  6. 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. https://doi.org/10.1021/ja00167a010
  7. 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. https://doi.org/10.1021/ja00007a006
  8. Harada, T.; Rudzinski, J. M.; Shinkai, S. J. Chem. Soc., PerkinTrans. 1992, 2, 2109.
  9. Harada, T.; Rudzinski, J. M.; Shinkai, S. Tetrahedron 1993, 49, 5941. https://doi.org/10.1016/S0040-4020(01)87180-5
  10. Harada, T.; Ohseto, F.; Shinkai, S.Tetrahedron 1994, 50, 13377. https://doi.org/10.1016/S0040-4020(01)89345-5
  11. 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. https://doi.org/10.1021/jo972134+
  12. Choe, J.-I.; Kim, K.; Chang, S.-K. Bull. Korean Chem. Soc.2000, 21, 465. https://doi.org/10.1007/BF02705436
  13. Choe, J.-I.; Chang, S.-K.; Ham, S. W.; Nanbu,S.; Aoyagi, M. Bull. Korean Chem. Soc. 2001, 22, 1248.
  14. Choe, J.-I.; Chang, S.-K.; Nanbu, S. Bull. Korean Chem. Soc. 2002, 23,891. https://doi.org/10.5012/bkcs.2002.23.6.891
  15. Choe, J.-I.; Lee, S. H.; Oh, D.-S. Bull. Korean Chem. Soc. 2004,25, 55. https://doi.org/10.5012/bkcs.2004.25.1.055
  16. 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. https://doi.org/10.1021/ja016526g
  17. 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. https://doi.org/10.1021/ja0259786
  18. Hong, B. H.; Bae, S. C.; Lee, C.-W.; Jeong,S.; Kim, K. S. Science 2001, 294, 348. https://doi.org/10.1126/science.1062126
  19. Kim, K. S. Curr. Appl. Phys. 2002, 2, 65. https://doi.org/10.1016/S1567-1739(01)00091-8
  20. Suh, S. B.; Hong, B. H.; Tarakeshwar, P.;Youn, S. J.; Jeong, S.; Kim, K. S. Phys. Rev. B 2003, 67, 241402(R). https://doi.org/10.1103/PhysRevB.67.241402
  21. Kim, K. S. Bull. Korean Chem. Soc. 2003, 24, 757. https://doi.org/10.1007/s11814-007-0038-2
  22. HyperChem Release 6.3; Hypercube, Inc.: Waterloo, Ontario,Canada, 2001.
  23. Minamino, S.; Choe, J.-I.; Chang, S.-K.; Mizutani, F.; Nanbu, S.Chem. Phys. Lett. 2003, 374, 572. https://doi.org/10.1016/S0009-2614(03)00753-X
  24. Gutsche, C. D.; Bauer, L. J. Tetrahedron Lett. 1981, 22, 4763. https://doi.org/10.1016/S0040-4039(01)92337-8

피인용 문헌

  1. Transportation behavior of alkali ions through a cell membrane ion channel. A quantum chemical description of a simplified isolated model vol.18, pp.8, 2012, https://doi.org/10.1007/s00894-012-1364-9
  2. Ab initio calculated structures of conformers for 1,3-dimethoxy-p-tert-butylcalix[4]crown-5-ether complexed with potassium cation vol.722, pp.1, 2005, https://doi.org/10.1016/j.theochem.2004.11.052