Theoretical study of inclusion complexation of 3-amino-5-nitrobenzisothiazole with β-cyclodextrin

Leila, Nouar; Sakina, Haiahem; Bouhadiba, Abdelaziz; Fatiha, Madi

doi:10.1016/j.molliq.2011.02.016

Cited by 15 publications

(3 citation statements)

References 29 publications

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“…The interaction energy (eq 4) is defined as the difference between the energy of the complex and the sum of the energies of both partners at their complex geometry. The deformation energy (eq 5) is determined by the difference between the energy of one of the partners of the complex and its energy at the complex geometry [30]. E CD in the complex is the single point energy value of CD in the optimized complex [31]–[34].…”

Section: Methodsmentioning

confidence: 99%

Enhanced Solubilisation of Six PAHs by Three Synthetic Cyclodextrins for Remediation Applications: Molecular Modelling of the Inclusion Complexes

et al. 2012

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Solubilisation of six polycyclic aromatic hydrocarbons (PAHs) (acenaphthene, anthracene, fluoranthene, fluorene, phenanthrene and pyrene) by three synthetic cyclodextrins (CDs) (2-hydroxypropyl-β-CD, hydroxypropyl-γ-CD and ramdomly methylated-β-CD) was investigated in order to select the CD which presents the greatest increase in solubility and better complexation parameters for its use in contaminated scenarios. The presence of the three cyclodextrins greatly enhanced the apparent water solubility of all the PAHs through the formation of inclusion complexes of 1∶1 stoichiometry. Anthracene, fluoranthene, fluorene and phenanthrene clearly presented a higher solubility when β-CD derivatives were used, and especially the complexes with the ramdomly methylated-β-CD were favoured. On the contrary, pyrene presented its best solubility results when using 2-hydroxypropyl-γ-CD, but for acenaphthene the use of any of the three CDs gave the same results. Complementary to experimental phase-solubility studies, a more in-depth estimation of the inclusion process for the different complexes was carried out using molecular modelling in order to find a correlation between the degree of solubilisation and the fit of PAH molecules within the cavity of the different CDs and to know the predominant driving forces of the complexation.

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Section: Methodsmentioning

confidence: 99%

Enhanced Solubilisation of Six PAHs by Three Synthetic Cyclodextrins for Remediation Applications: Molecular Modelling of the Inclusion Complexes

et al. 2012

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“…The interaction and deformation energy (DEF) for each host and guest component during complex formation is the difference between the optimized component compared to its energy in the complex (Eq. ( 2)) [49]:…”

Section: Page 3/19mentioning

confidence: 99%

Computational investigation of dimethoate and β-cyclodextrin inclusion complex: molecular structures, intermolecular interactions, and electronic analysis

et al. 2023

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The proposed study concerns the inclusion complexation of dimethoate (DMT) in the β-cyclodextrin (β-CD) molecule cage using a 1:1 stoichiometry. The interactions between DMT and -CD were evaluated using PM7 and DFT in water and gas with base 6-31G(d,p); using the CAMB3LYP functional.All approaches agree with the optimal 3D structure, which includes full DMT inclusion in the CD cavity. Complexation, LUMO, and HOMO energies were computed. The natural bond orbital (NBO) and UV-visible calculations were determined and discussed. Additionally, the non-covalent intermolecular interactions between dimethoate and β-cyclodextrin are investigated through: reduced density gradient (RDG), non-covalent interaction (NCI) and independent gradient model (IGM) that the main forces stabilizing the examined inclusion complex are H-bond and Van Der Waals interactions. Furthermore, the energy decomposition analysis (EDA) emphasizes the importance of the H-bond as attractive interactions.

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“…[7][8][9][10][11] Some irregular energy differences in the interactions between enantiomers and selectors were found by using various molecular modeling methods. [12][13][14][15][16][17] Nevertheless, because of the computational limitations of low levels of theory, or the non-quantitative nature of theoretical studies with respect to qualitative analyses, the results of previous studies could only be used to interpret the mechanism of enantiomeric separation, but could not be used to predict the possibility of separation before the CE experiment.…”

Section: Introductionmentioning

confidence: 99%

Quantitative prediction of enantioseparation using β-cyclodextrin derivatives as chiral selectors in capillary electrophoresis

Guo

Wang

Zuo

et al. 2014

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β-Cyclodextrin derivatives as chiral selectors are becoming increasingly important for enantioseparations in capillary electrophoresis (CE). Nevertheless, there are some enormous challenges in choosing effective selectors from a variety of compounds, and up to now no systematic quantitative studies for predicting the possibility of enantiomeric separation before CE experiments have been reported. In this paper, in order to resolve previous confusions, we investigated the enantioseparations of ten chiral drugs using a method of combining experiments with theoretical calculations. MMFF, PM3, DFT and ONIOM2 methods were simultaneously utilized during the course of our computer simulations. The results indicated that a specific value of greater than or approximately equal to 6 kJ mol(-1) for the interaction energy difference (ΔΔE) between a pair of enantiomers with a selector is required in order to achieve enantiomeric separation. This discovery offers a meaningful reference to predict enantiomeric separations, so as to design and synthesize some more efficient chiral selectors.

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Theoretical study of inclusion complexation of 3-amino-5-nitrobenzisothiazole with β-cyclodextrin

Cited by 15 publications

References 29 publications

Enhanced Solubilisation of Six PAHs by Three Synthetic Cyclodextrins for Remediation Applications: Molecular Modelling of the Inclusion Complexes

Enhanced Solubilisation of Six PAHs by Three Synthetic Cyclodextrins for Remediation Applications: Molecular Modelling of the Inclusion Complexes

Computational investigation of dimethoate and β-cyclodextrin inclusion complex: molecular structures, intermolecular interactions, and electronic analysis

Quantitative prediction of enantioseparation using β-cyclodextrin derivatives as chiral selectors in capillary electrophoresis

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