Comparative study of calix[4]arene derivatives: implications for ligand design

Hong, Jooyeon; Ham, Sihyun

doi:10.1016/j.tetlet.2008.02.061

Cited by 12 publications

(13 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…10 Due to our previous DFT calculation at the MPWB1K/6-311G**//B3LYP/6-311G** level, the 1,3-alternate of 2 is located to be 10.1 kcal/mol higher in energy than that of the cone. 9 The conformation of 3 was reported to be 1,3-alternate by NMR 10,11 and X-ray 10 studies presumably due to the preferential dipole moment. In Figure 2, the computed global minimum structure (A) and X-ray structure (B) for 3 are displayed.…”

Section: Resultsmentioning

confidence: 99%

“…9 The first synthesis of 3 was reported in 2001 and X-ray diffraction study revealed that 3 adopts a 1,3-alternate conformation in the solid state. 10 Due to our previous DFT calculation at the MPWB1K/6-311G**//B3LYP/6-311G** level, the 1,3-alternate of 2 is located to be 10.1 kcal/mol higher in energy than that of the cone.…”

Section: Resultsmentioning

confidence: 99%

“…[3][4][5][6][7][8][9] Thiacalix[4]-arene can adapt four distinctive conformations as cone, partial cone, 1,2-alternate, and 1,3-alternate, as in the case of calix [4]arene. The different conformations of 2 can be executed by appropriate functionalization.…”

Section: Introductionmentioning

confidence: 99%

“…11,12,18 Conformational characteristics and thermodynamics stability order among different conformers of 2 were previously reported by us in comparison with those of 1 by using density functional theory (DFT) calculations. 9 Despite of the phenomenological behavior of the metal ion shuttling with 3, no detailed structural and complexation studies were reported on 3 and its metal ion complexes.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Molecular Dynamics Simulation and Density Functional Theory Investigation for Thiacalix[4]biscrown and its Complexes with Alkali-Metal Cations

Hong¹,

Lee²,

Ham

2010

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

The structural and energetic preferences of thiacalix [4]biscrown-5 with and without alkali metal ions (Na + , K + , Rb + , and Cs + ) have been theoretically investigated for the first time using molecular dynamic (MD) simulations and density functional theory (MPWB1K/6-31G(d)//B3LYP/6-31G(d)) methods. The formation of the metal ion complex by the host is mainly driven by the electrostatic attraction between crown-5 oxygens and a cation together with the minor contribution of the cation-π interaction between two facing phenyl rings around the cation. The computed binding energies and the atomic charge distribution analysis for the metal binding complexes indicate the selectivity toward a potassium ion. The theoretical results herein explain the experimentally observed extractability order by this host towards various alkali metal ions. The physical nature and the driving forces for cation recognition by this host are discussed in detail.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Molecular Dynamics Simulation and Density Functional Theory Investigation for Thiacalix[4]biscrown and its Complexes with Alkali-Metal Cations

Hong¹,

Lee²,

Ham

2010

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

show abstract

“…25,26 Recently, the comparative theoretical study of three parent calix [4]arene analogues (calix [4]arene, thiacalix [4]arene, and homooxacalix [4]arene) has been performed using molecular dynamic simulations and density functional theory (DFT) methods. 27 In this study, we have optimized the conformational isomers of p-tert-butylthiacalix [4]crown-5-ether (3) by using the DFT B3LYP/6 -31 + G (d,p) and mPW1PW91/6 -31 + G(d,p) (hybrid HF-DF) calculation methods. The primary objective of this research is to determine the relative stability of the different conformational isomers for 3 by using the improved mPW1PW91/6 -31 + G(d,p) calculation method.…”

Section: Journal Of the Korean Chemical Societymentioning

confidence: 99%

mPW1PW91 Calculated Relative Stabilities and Structures for the Conformers of 1,3-dimethoxy-p-tert-butylthiacalix[4]crown-5-ether

2009

Journal of the Korean Chemical Society

View full text Add to dashboard Cite

ABSTRACT. Molecular structures of the various conformers for the 1,3-dimethoxy-p-tert-butylthiacalix[4] crown-5-ether (3) were optimized by using DFT B3LYP/6 -31 + G(d,p) and mPW1PW91/6 -31 + G(d,p) (hybrid HF-DF) calculation methods. We have analyzed the energy differences and structures of eight in/out orientations (cone_oo, cone_oi, pc_oo, pc_io, pc_oi, pc_ii, 13a_oo, 13a_io) of two methoxy groups in three major conformations (cone, partial-cone and 1,3-alternate). The 13a_oo (out-out orientation of the 1,3-alternate conformer) is calculated to be the most stable among eight different conformations of 3, and in accord with the experimental result. The ordering of relative stability resulted from the mPW1PW91/6 -31 + G(d,p) calculation method is following: 13a_oo > 13a_io∼pc_io∼cone_oo > cone_oi∼pc_oo∼pc_oi > pc_ii.

show abstract

A Study of the Modification of the Gold Electrode Surface with a Calix[4]arene Self‐Assembled Monolayer

et al. 2010

View full text Add to dashboard Cite

Substituted calix [4]arene molecules were used to modify the gold disk electrode surface and the electrochemical properties of this electrode were compared with those of the bare electrode. Cyclic voltammetry measurements permitted the calculation of a Langmuir-type adsorption isotherm for the formation of the calixarene SAM. The calixarene adsorption from chloroform solution appeared to be more effective, compared to the adsorption from DMF solution, but the process was less reproducible. Preliminary results, obtained by the atomic force microscopy measurements, indicate that the calixarene molecules form a stable monolayer on the Au(111) surface and the SAM structure depends on the solvent used. Impedance measurements demonstrate that the capacity of the modified electrode varies in the presence of ions, depending on their size and shape; this can potentially be utilized in designing ion-selective sensors.

show abstract

Comparative study of calix[4]arene derivatives: implications for ligand design

Cited by 12 publications

References 39 publications

Molecular Dynamics Simulation and Density Functional Theory Investigation for Thiacalix[4]biscrown and its Complexes with Alkali-Metal Cations

Molecular Dynamics Simulation and Density Functional Theory Investigation for Thiacalix[4]biscrown and its Complexes with Alkali-Metal Cations

mPW1PW91 Calculated Relative Stabilities and Structures for the Conformers of 1,3-dimethoxy-p-tert-butylthiacalix[4]crown-5-ether

A Study of the Modification of the Gold Electrode Surface with a Calix[4]arene Self‐Assembled Monolayer

Contact Info

Product

Resources

About