Bulletin of the Korean Chemical Society

  • 제24권1호
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  • Pages.75-80
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  • 2003
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Ab Initio Study of the Complexation Behavior of Calix[5]arene Derivative toward Alkyl Ammonium Cations

  • 발행 : 2003.01.20
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초록

The structures and complexation energies of penta-O-alkylated 1b and penta-O-tert-butyl ester 1e of p-tert-butylcalix[5]arene and their simplified structures (2b and 2e) toward a series of alkyl ammonium guests have been calculated by a semi-empirical AM1 method. For AM1 calculations, complexation efficiencies of the simplified host 2e are very similar to the values of host 1e. The complexes of simplified host 2e with alkyl ammonium ions also have been optimized by ab initio HF/6-31G method. The calculated complexation efficiencies for 2e by ab initio method have been found to be bigger in magnitude than the values obtained by AM1 calculations for linear alkyl ammonium guests. Calculation results show that all of the calix[5]aryl derivatives investigated in this study have much better complexation ability toward ammonium cation without alkyl group compared with other alkyl ammonium guests. Ab initio calculations also well duplicate the molecular discriminating behaviors of calix[5]arene derivative 2e between butyl ammonium ions: $n-BuNH_3^+\;>\;iso-BuNH_3^+\;>\;sec-BuNH_3^+\;>\;tert-BuNH_3^+$.

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피인용 문헌

  1. Recent Application of ab initio Calculations on Calixarenes and Calixarene Complexes. A Review vol.69, pp.6, 2004, https://doi.org/10.1135/cccc20041169
  2. Ab Initio Study of the Complexation Behavior of p-tert-Butylcalix[5]arene Derivative toward Alkyl Ammonium Cations vol.25, pp.2, 2003, https://doi.org/10.5012/bkcs.2004.25.2.190
  3. Structure of p-Phenylcalix[5]arene Dichloroform Solvate vol.26, pp.2, 2005, https://doi.org/10.5012/bkcs.2005.26.2.337
  4. Ab Initio Study of the Complexation Behavior of Calix[6](aza)cryptand with Alkyl Ammonium Cations vol.26, pp.4, 2003, https://doi.org/10.5012/bkcs.2005.26.4.645
  5. DFT Conformational Study of Calix[5]arene and Calix[4]arene: Hydrogen Bond vol.29, pp.10, 2008, https://doi.org/10.5012/bkcs.2008.29.10.1893
  6. 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
  7. A DFT study on a calix[5]crown-based heteroditopic receptor vol.22, pp.6, 2003, https://doi.org/10.1080/10610271003678529