Bulletin of the Korean Chemical Society

  • 제30권4호
  • /
  • Pages.837-845
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  • 2009
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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DFT Conformational Study of Calix[6]arene: Hydrogen Bond

  • 발행 : 2009.04.20
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초록

We have performed DFT calculations to investigate the conformational characteristics and hydrogen bonds of the calix[6]arene (1) and p-tert-butylcalix[6]arene (2). The structures of various conformers of 1 were optimized by using the B3LYP/6-31G(d,p) and /6-31+G(d,p) methods followed by single point calculation of MPW1PW91/ 6-31G(d,p). The relative stability of the conformers of 1 is in the following order: cone (pinched: most stable) > partial-cone > cone (winged) $\sim$ 1,2-alternate $\sim$ 1,2,3-alternate > 1,4-alternate > 1,3-alternate > 1,3,5-alternate. The structures of different conformers of 2 were optimized by using the B3LYP/6-31G(d,p) method followed by single point calculation of MPW1PW91/6-31G(d,p). The relative stability of the conformers of 2 is in the following order: cone (pinched) > 1,2-alternate > cone (winged) > 1,4-alternate $\sim$ partial-cone > 1,2,3-alternate > 1,3,5alternate > 1,3-alternate. One of the important factors affecting the relative stabilities of the various conformers of the 1 and 2 is the number and strength of the intramolecular hydrogen bonds.

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  2. H-NMR) and Theoretical Approaches vol.83, pp.5, 2014, https://doi.org/10.1111/cbdd.12267
  3. Relay proton transfer triggered twisted intramolecular charge transfer vol.14, pp.12, 2015, https://doi.org/10.1039/C5PP00339C
  4. Influence of polyether chain on the non-covalent interactions and stability of the conformers of calix[4]crown ethers vol.91, pp.1-2, 2018, https://doi.org/10.1007/s10847-018-0801-5
  5. mPW1PW91 Calculated Conformational Study of Calix[n]arene (n = 4,5,6): Hydrogen Bond vol.53, pp.6, 2009, https://doi.org/10.5012/jkcs.2009.53.6.640
  6. A theoretical study of the conformational preference of alkyl- and aryl-substituted pyrogallol[4]arenes and evidence of the accumulation of negative electrostatic potential within the cavity of their vol.40, pp.4, 2009, https://doi.org/10.1080/08927022.2013.806806
  7. Winged-Cone Conformation in Hexa-p-tert-butylcalix[6]arene Driven by the Unusually Strong Guest Encapsulation vol.2, pp.8, 2009, https://doi.org/10.1021/acsomega.7b00900