Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Ab Initio Calculated Structures and Vibrational Spectra of 1,3-Diethoxy-p-tert-butylcalix[4]crown-5-ether Complexed with Potassium Cation

  • Published : 2007.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

Molecular structures were optimized for the 1,3-diethoxycalix[4]crown-5-ether (2) in the various isomers and their potassium-ion complexes by using B3LYP/6-31+G(d,p)//B1LYP/6-31G(d,p) method after ab initio RHF/6-31G calculation. The cone-shaped isomer of 2 with cr-binding mode has shown the strongest binding efficiency among the six different complexes attributed to seven electrostatic interactions between the potassium cation and the oxygen atoms of crown-5-ether and ethoxy groups of the host (2). The vibrational spectra of 2 and its K+-complexes were obtained by restricted Hartree-Fock (RHF) calculations with the 6-31G basis set. The characteristic vibrational frequencies of various C-O-C stretching and bending motions are analyzed.

Keywords

References

  1. Dijkstra, P. J.; Brunink, J.; Bugge, K.-E.; Reinhoudt, D. N.; Harkema, S.; Ungaro, R.; Ugozzoli, F.; Ghidini, E. J. Am. Chem. Soc. 1989, 111, 7567
  2. Reinhoudt, D. N.; Dijkstra, P. J.; in't Veld, P. J. A.; Bugge, K.-E.; Harkema, S.; Ungaro, R.; Ghidini, E. J. Am. Chem. Soc. 1987, 109, 4761
  3. Van Loon, J.-D.; Arduini, A.; Verboom, W.; Ungaro, R.; van Hummel, G. J.; Harkema, S.; Reinhoudt, D. N. Tetrahedron Lett. 1989, 30, 2681
  4. Ghidini, E.; Ugozzoli, F.; Ungaro, R.; Harkema, S.; El-Fadl, A. A.; Reinhoudt, D. N. J. Am. Chem. Soc. 1990, 112, 6979
  5. Lauterbach, M.; Wipff, G. In Physical Supramolecular Chemistry; Echegoyen, L.; Kaifer, A. E., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1996; pp 65-102
  6. Bernardino, R. J.; Cabral, C. Supramol. Chem. 2002, 14, 57 https://doi.org/10.1080/10610270290006574
  7. Computational Approaches in Supramolecular Chemistry; Wipff, G., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994
  8. Choe, J.-I.; Chang, S.-K.; Ham, S. W.; Nanbu, S.; Aoyagi, M. Bull. Korean Chem. Soc. 2001, 22, 1248
  9. 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
  10. Choe, J.-I.; Oh, D.-S. Bull. Korean Chem. Soc. 2004, 25, 847 https://doi.org/10.5012/bkcs.2004.25.6.847
  11. Choe, J.-I.; Chang, S.-K.; Lee, S.; Nanbu, S. J. Mol. Struct. (Theochem) 2005, 722, 117 https://doi.org/10.1016/j.theochem.2004.11.052
  12. HyperChem Release 7.5; Hypercube, Inc.: Waterloo, Ontario, Canada, 2002
  13. Choe, J.-I.; Kim, K.; Chang, S.-K. Bull. Korean Chem. Soc. 2000, 21, 465
  14. 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
  15. Exploring Chemistry with Electronic Structure Methods, 2nd Ed.; Foresman, J. B.; Frisch, A. Gaussian Inc.: Pittsburgh, PA, 1996
  16. Nicholas, J. B.; Hay, B. P. J. Phys. Chem. A 1999, 103, 9815 https://doi.org/10.1021/jp990570p
  17. Cram, D. J.; Lein, G. M. J. Am. Chem. Soc. 1985, 107, 3657 https://doi.org/10.1021/ja00298a041
  18. Chem3D, Version 7.0; Cambridge Soft: Cambridge, MA, U.S.A., 2001

Cited by

  1. PW1PW91-Calculated Structures, IR Spectra, and Frontier Orbitals of 1,2-Bridged Calix[4]aryl Picrate Complexed with Alkali Metal Ions vol.36, pp.5, 2015, https://doi.org/10.1002/bkcs.10289
  2. DFT Study for p-tert-Butylcalix[4]arene Crown Ether Bridged at the Lower Rim with Pyridyl Unit Complexed with Potassium Ion vol.28, pp.12, 2007, https://doi.org/10.5012/bkcs.2007.28.12.2310
  3. Cesium Selective Calix[6]arene Bisbridged Receptor vol.29, pp.1, 2007, https://doi.org/10.5012/bkcs.2008.29.1.211
  4. Physical Chemistry Research Articles Published in the Bulletin of the Korean Chemical Society: 2003-2007 vol.29, pp.2, 2008, https://doi.org/10.5012/bkcs.2008.29.2.450
  5. DFT Study for Azobenzene Crown Ether p-tert-Butylcalix[4]arene Complexed with Alkali Metal Ion vol.29, pp.3, 2008, https://doi.org/10.5012/bkcs.2008.29.3.541
  6. DFT Study for Cage-annulated p-tert-Butylcalix[4]crown-ether Complexed with Potassium Ion vol.29, pp.7, 2007, https://doi.org/10.5012/bkcs.2008.29.7.1374
  7. 1,3-디메톡시-티아캘릭스[4]크라운-5-에테르의 이형체들의 상대적인 안정성과 구조들에 대한 mPW1PW91 계산 연구 vol.53, pp.5, 2007, https://doi.org/10.5012/jkcs.2009.53.5.521