Study of complex formation between β-cyclodextrin and benzene

Trofymchuk, Iryna M.; Belyakova, L. A.; Grebenyuk, A. G.

doi:10.1007/s10847-010-9757-9

Cited by 26 publications

(17 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This is in very good agreement with the experimental value from [34]. All our other complex conformers have positive Δ E complexation values, up to BCDbenzeneverticalO23lO6r with +9.69 kcal mol −1 , and thus are endothermic, Table 3.…”

Section: Resultssupporting

confidence: 90%

“…At 280 K and 290 K these events appeared earlier, at 140 ps/160 ps and 50 ps/125 ps, respectively. This was in good qualitatively agreement with the complex formation constants that were experimentally determined from UV spectra in [34] and showed that the complex was more stable at lower temperatures. At 300 K benzene tried to leave the cavity early at the O6 side, but always returned.…”

Section: Resultssupporting

confidence: 89%

“…Our calculated AM1 HOMO/LUMO gaps of empty β-CD conformers, of benzene D 6 h (Table 1) and the eight complexes (Table 3) are of the same order of magnitude as the values calculated with PM3 in the literature [34] where they found for β-CD 12.44 eV, for benzene 10.15 eV and for the β-CD/benzene complex 10.15 eV. These authors found β-CD/benzene of 1:1 inclusion type in aqueous solution by experimental UV absorption spectra with various concentrations of β-CD.…”

Section: Resultssupporting

confidence: 70%

See 2 more Smart Citations

The β-cyclodextrin/benzene complex and its hydrogen bonds – a theoretical study using molecular dynamics, quantum mechanics and COSMO-RS

Köhler¹,

Grczelschak-Mick²

2013

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryFour highly ordered hydrogen-bonded models of β-cyclodextrin (β-CD) and its inclusion complex with benzene were investigated by three different theoretical methods: classical quantum mechanics (QM) on AM1 and on the BP/TZVP-DISP3 level of approximation, and thirdly by classical molecular dynamics simulations (MD) at different temperatures (120 K and 273 to 300 K). The hydrogen bonds at the larger O2/O3 rim of empty β-CDs prefer the right-hand orientation, e.g., O3-H…O2-H in the same glucose unit and bifurcated towards …O4 and O3 of the next glucose unit on the right side. On AM1 level the complex energy was −2.75 kcal mol−1 when the benzene molecule was located parallel inside the β-CD cavity and −2.46 kcal mol−1 when it was positioned vertically. The AM1 HOMO/LUMO gap of the empty β-CD with about 12 eV is lowered to about 10 eV in the complex, in agreement with data from the literature. AM1 IR spectra displayed a splitting of the O–H frequencies of cyclodextrin upon complex formation. At the BP/TZVP-DISP3 level the parallel and vertical positions from the starting structures converged to a structure where benzene assumes a more oblique position (−20.16 kcal mol−1 and −20.22 kcal mol−1, resp.) as was reported in the literature. The character of the COSMO-RS σ-surface of β-CD was much more hydrophobic on its O6 rim than on its O2/O3 side when all hydrogen bonds were arranged in a concerted mode.This static QM picture of the β-CD/benzene complex at 0 K was extended by MD simulations. At 120 K benzene was mobile but always stayed inside the cavity of β-CD. The trajectories at 273, 280, 290 and 300 K certainly no longer displayed the highly ordered hydrogen bonds of β-CD and benzene occupied many different positions inside the cavity, before it left the β-CD finally at its O2/O3 side.

show abstract

Section: Resultssupporting

confidence: 90%

Section: Resultssupporting

confidence: 89%

Section: Resultssupporting

confidence: 70%

See 1 more Smart Citation

The β-cyclodextrin/benzene complex and its hydrogen bonds – a theoretical study using molecular dynamics, quantum mechanics and COSMO-RS

Köhler¹,

Grczelschak-Mick²

2013

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Figure 8 exhibits the schematic presentation for electron transfer from photo-excited -CD to conduction band of ZnS NPs. It is known that the -CD has high LUMO level (1.44 eV) 11 as compared to conduction band of ZnS NPs (−1 9 eV). Therefore, a photo induced electron transfer takes place easily from -CD to conduction band of ZnS NPs, which results in quenching of luminescence of CTAB stabilized nanoparticles (Fig.…”

Section: Resultsmentioning

confidence: 99%

A Mechanistic Study of Photoluminescence Quenching of Cetyl Trimethyl Ammonium Bromide Stabilized ZnS Nanoparticles with β-Cyclodextrin

Mehta¹,

Khushboo²,

Kumar³

2012

j nanosci nanotechnol

View full text Add to dashboard Cite

This paper reports a mechanistic study of photoluminescence (PL) quenching of cetyl trimethyl ammonium bromide (CTAB) stabilized ZnS nanoparticles (NPs) on surface modification with beta-cyclodextrin (beta-CD). The surface functionalization of NPs has been achieved due to the formation of inclusion complex between beta-CD and hydrophobic tail of CTAB. It has been observed that quenching takes place in the PL intensities of NPs on the addition of beta-CD. Therefore, an attempt has been made to understand mechanism for these quenching phenomena. The detailed studies reveal that the beta-CD causes PL quenching due to the electron transfer between NPs and beta-CD and aggregation of NPs.

show abstract

“…It was shown that β-CD and aromatic compounds could form "host -guest" inclusion complexes in aqueous solutions. The formation of "β-CD -aromatic compound" complexes is spontaneous and thermodynamically profitable exothermal process [32,33]. The equilibrium adsorption study was used to evaluate the role of cyclic oligosaccharide fragments as specific adsorption sites of ordered CD-MCM-41 silicas.…”

Section: Displays Isotherms Of Nitrogen Adsorption-desorption and Pormentioning

confidence: 99%

β-cyclodextrin-MCM-41 silica as promising adsorbent for the trace amounts removal of aromatics from water

Trofymchuk¹,

Roik²,

Belyakova³

2016

Him. Fiz. Tehnol. Poverhni

View full text Add to dashboard Cite

show abstract

Study of complex formation between β-cyclodextrin and benzene

Cited by 26 publications

References 17 publications

The β-cyclodextrin/benzene complex and its hydrogen bonds – a theoretical study using molecular dynamics, quantum mechanics and COSMO-RS

The β-cyclodextrin/benzene complex and its hydrogen bonds – a theoretical study using molecular dynamics, quantum mechanics and COSMO-RS

A Mechanistic Study of Photoluminescence Quenching of Cetyl Trimethyl Ammonium Bromide Stabilized ZnS Nanoparticles with β-Cyclodextrin

β-cyclodextrin-MCM-41 silica as promising adsorbent for the trace amounts removal of aromatics from water

Contact Info

Product

Resources

About