Host-guest complex of N-(2-chloroethyl), N-nitroso, N′, N′ -dicyclohexylsulfamid with β-cyclodextrin: Fluorescence, QTAIM analysis and structure-chemical reactivity

Bensouilah, Nadjia; Fisli, Hassina; Bensouilah, Hamza; Zaater, Sihem; Abdaoui, Mohamed; Boutemeur-Kheddis, Baya

doi:10.1016/j.molstruc.2017.05.135

Cited by 17 publications

(10 citation statements)

References 28 publications

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“…These results are consistent with QTAIM analyses performed for other guest-host complexes, [34][35][36] although in our work, a different criterion for the classication of the interactions was used.…”

Section: Qtaim Analysissupporting

confidence: 91%

“…The results obtained for the molecular inclusion complexes formed with b-CD are in agreement with other DFT studies. 30,32,35,36 As in the present work, predominant partial occlusion is observed when b-CD is the host molecule.…”

Section: Renement Of the Representative Structures Using Dft M06-2xsupporting

confidence: 75%

“…Particularly, the molecular inclusion complexes formed between the CDs and different molecules have been studied by several computational methods, including molecular docking, 28,29 molecular dynamics, 30,31 density functional theory (DFT) calculations, [31][32][33] and natural bonding orbitals and quantum theory of atoms in molecules approaches. [34][35][36] However, in these studies, the authors directly set the molecule of interest in contact with the interior of the CD cavity in certain congurations, based largely on chemical intuition. Also, generally, only b-CD is considered as a host molecule; this ignores the possibility of better encapsulation capacities of other CDs, especially g-CD.…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of the molecular inclusion process of β-hexachlorocyclohexane in cyclodextrins

et al. 2019

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Section: Qtaim Analysissupporting

confidence: 91%

Section: Renement Of the Representative Structures Using Dft M06-2xsupporting

confidence: 75%

Section: Introductionmentioning

confidence: 99%

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Evaluation of the molecular inclusion process of β-hexachlorocyclohexane in cyclodextrins

et al. 2019

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“…No new covalent bonds were formed during the complexing process of TBZ and HP β CD. It is confirmed that the binding of TBZ with HPβCD was through intermolecular forces, such as hydrogen bonds, van der waals forces, etc 39 …”

Section: Resultsmentioning

confidence: 80%

Encapsulation of thiabendazole in hydroxypropyl‐β‐cyclodextrin nanofibers via polymer‐free electrospinning and its characterization

Gao

Liu

Jiang

et al. 2020

Pest Management Science

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BACKGROUNDThiabendazole (TBZ) is a poorly water‐soluble benzimidazole fungicide. However, the water solubility of TBZ can be significantly enhanced by inclusion complexation with cyclodextrins. In this study, a thiabendazole/hydroxypropyl‐β‐cyclodextrin (TBZ/HPβCD) complex was synthesized and electrospinning was performed to produce a TBZ/HPβCD nanofibrous (TBZ/HPβCD‐NF) complex that improved water solubility and antifungal activity.RESULTSThe formation of TBZ/HPβCD‐NF was characterized by Fourier transform infrared spectroscopy, X‐ray diffraction and nuclear magnetic resonance. The morphology of TBZ/HPβCD‐NF was studied by scanning electron microscopy. A phase solubility experiment showed that HPβCD exerted a great solubilization effect on TBZ, and TBZ/HPβCD‐NF had better antifungal activity compared to that of TBZ alone.CONCLUSIONSIn summary, the solid fungicidal nanodispersion prepared in the present study is a new type of formulation that can enhance the water solubility of TBZ. This formulation, which demonstrated potential as a new fast dissolving formulation type with increased efficacy, is expected to be conducive to the sustainable development of agriculture. © 2020 Society of Chemical Industry

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“…The interaction energy for different intramolecular interactions was calculated by using Espinosa‐Molins‐Lecomte (EML) relationship as following I. E.=0.5V b , where V b is local potential energy density at the BCP . The calculated intramolecular hydrogen bonding energy is in the range of 49.08‐71.80 kJ/mol, (Table ). Based on the topology parameters, weak intramolecular hydrogen bonding is found in L 2 , while medium intramolecular hydrogen bonding is in L 1 and L 3 .…”

Section: Resultsmentioning

confidence: 99%

Chemical Reactivity and Quantifying the Intra‐ and Intermolecular Interactions in Zwitterionic Compounds

2018

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A zwitterionic Schiff base, (E)-2-((2-(1-hydroxyethyl)phenyliminio)methyl-6-methoxyphenolate (L 1 ) was prepared and fully characterized by spectral methods. The crystal structure was determined by using single crystal X-ray diffraction study. Inter and intra-molecular interactions in L 1 and similar zwitterionic Schiff bases (L 2 = (E)-2-(((2hydroxyethyl)iminio)phenyl)methyl-5-(prop-2yn-1-yloxy)phenolate and L 3 = (E)-2-(2-hydroxy-3methoxybenzylideneammonio)-3-(1H-imidazol-3-ium-4-yl) propanoate) have been established via topological analysis by considering the presence of (3,-1) bond critical points (BCP) between the interacting atoms using the approach of QTAIM (Quantum Theory of Atoms In Molecules) with the aid of ADF (Amsterdam Density Functional) 2017 package. Furthermore, Hirshfeld 2D fingerprint plots and 3D deformation densities were used to determine the interactions quantitatively. The L 1 -L 3 forms a six-member pseudo cycle via an intramolecular N-H···O hydrogen bond, and the crystal structure is further stabilized by the presence of p···p stacking interactions. The effect of hydrogen bonding interactions of the molecule on infra red frequencies has been studied using DFTB (Density Functional based Tight Binding) method with ADF. The effect of intermolecular interactions of these compounds towards biomolecules was studied by using Auto Dock Vina and QTAIM analysis.

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Host-guest complex of N-(2-chloroethyl), N-nitroso, N′, N′ -dicyclohexylsulfamid with β-cyclodextrin: Fluorescence, QTAIM analysis and structure-chemical reactivity

Cited by 17 publications

References 28 publications

Evaluation of the molecular inclusion process of β-hexachlorocyclohexane in cyclodextrins

Evaluation of the molecular inclusion process of β-hexachlorocyclohexane in cyclodextrins

Encapsulation of thiabendazole in hydroxypropyl‐β‐cyclodextrin nanofibers via polymer‐free electrospinning and its characterization

Chemical Reactivity and Quantifying the Intra‐ and Intermolecular Interactions in Zwitterionic Compounds

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