Stability and spatial arrangement of the 2,4-dichlorophenoxyacetic acid and β-cyclodextrin inclusion compound: A theoretical study

Pereira, Robson Augusto; Anconi, Cléber P. A.; Nascimento, Clébio S.; Almeida, Wagner B. De; Santos, Hélio F. Dos

doi:10.1016/j.cplett.2015.05.044

Cited by 13 publications

(4 citation statements)

References 27 publications

(29 reference statements)

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“…The solvent effect plays a primary role in determining the stability of the inclusion compounds in the solution. The values of such contribution (𝜕∆𝐺 𝑖 𝑠𝑜𝑙𝑣 ), usually positive [22] (see also Table 2) are surprisingly negative for the AF-I@HP-β-CD and, as will be discussed with the equilibrium geometries, play a role in the inclusion orientation. Despite some negative 𝜕∆𝐺 𝑖 𝑠𝑜𝑙𝑣 computed for AF@HP-β-CD-00 (ID A) and AF@HP-β-CD-02 (ID A), the solvation contributes more significantly to the stabilization of the AF-I@HP-β-CD (00, 01, and 02), determining the preference or higher binding constant when compared to the AF@HP-β-CD systems.…”

Section: Gfn2-xtb Qc Studymentioning

confidence: 86%

“…Focusing on the pure QC approach, we found in the contributions [18,19] an innovative protocol to describe molecular recognition by CD, in which the semiempirical calculations were carried out for many distinct starting points. Regarding more sophisticated QC methods, density functional theory (DFT) has been applied for chiral recognition by modified CD [20] and other studies concerning CD-based systems [21][22][23]. More recently, the tight-binding QC method (GFN2-xTB) [24,25] has been applied to CD-based systems [26,27].…”

Section: Introductionmentioning

confidence: 99%

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Structure, stability, and dynamics of the inclusion complexes formed by auranofin derivatives and hydroxypropyl-β-cyclodextrin

Santos,

Anconi

2024

Preprint

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The inclusion compounds of auranofin (AF) and its iodide derivative (AF-I) with HP-b-CD were recently identified and characterized experimentally. In the present work, classical molecular dynamics and quantum computational GFN2-xTB method were applied to investigate the inclusion processes. As a result, both approaches addressed the AF-I@HP-β-CD as the most favorable system, as observed experimentally. The higher stability of AF-I@HP-β-CD was explained by entropy and solvation factors, with the GFN2-xTB method providing stability constant (logK1:1) in good agreement with experiment: 0.21 – 1.21 for AF@HP-β-CD and 1.31 – 2.33 for AF-I@HP-β-CD (experimental values are 1.48 and 2.52, respectively). The preferred inclusion mode for AF-I@HP-β-CD has the triethylphosphine (-PEt3) group pointed toward the head portion of the HP-β-CD where the hydroxypropyl groups are attached (labeled as P2). The P2 mode showed short contacts between -CH2CH3 groups (-PEt3) and -H3 only (inside the CD cavity), which is also supported by ROESY experiments.

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Section: Gfn2-xtb Qc Studymentioning

confidence: 86%

Section: Introductionmentioning

confidence: 99%

Structure, stability, and dynamics of the inclusion complexes formed by auranofin derivatives and hydroxypropyl-β-cyclodextrin

Santos,

Anconi

2024

Preprint

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“…The Stability and spatial arrangement of this complex reportead by Cleber P.A. Anconi et.al was successfully developed to enhance the phenoxy solubility [37]. Solubility may be effective in increasing degradation efficiency.…”

Section: Promotion Effects Of β-Cd On the Photodegradation Of 24-dmentioning

confidence: 99%

“…It is important to consider this issue from an environmental point of view, that with uncontrolled use of this herbicide, its presence in the environment and ecosystems causes soil, surface and groundwater contamination [37] and consequently it can enter the food chain, hence, using of the photoreactor can reduce the pollution significantly.…”

Section: The Impact Of Circulated-mode Photoreactor On the Photodegradation Of High Concentration 24-dmentioning

confidence: 99%

Study of visible-light photocatalytic degradation of 2,4-dichlorophenoxy acetic acid in batch and circulated-mode photoreactors

Safa

Mirzaei

Kazemi

et al. 2019

J Environ Health Sci Engineer

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Purpose The consumption of pesticides and chemical fertilizers is one of the major environmental and health problems. In this report, 2,4-dichlorophenoxyacetic acid (2,4-D) was chosen to evaluate the impact of photodegradation using LED (Lightemitting diode) (400 and 365 nm) sources in batch and programmable circulated-mode photoreactors respectively. Methods A β-cyclodextrin (β-CD) grafted titanium dioxide P25 (P25/β-CD) and complexation of 2,4-D and β-CD were synthesized via photoinduced and spray-drying methods, respectively. The structures were characterized. Moreover, we investigated the effects of the amount of catalyst, the β-CD amount on bed catalyst, irradiation time, kind of photoreactor on the photocatalytic degradation efficiency. Results Based on the results of experiments in batch reactor, the optimum amount of TiO 2 , β-CD grafted by catalyst were 1 and 0.1 g/L, respectively. In batch-mode the photodegradation efficiency of 2,4-D after 5 h with P25, P25/β-CD as a photocatalyst and 2,4-D/β-CD complex with P25 photocatalyst were approximately 81, 85 and 95% respectively. After 8 h of irradiation in circulated-mode reactor, degradation yields with P25, P25/β-CD and 2,4-D/β-CD complex along with P25 were 89, 91 and 96% respectively. On the other hand, the circulated-mode photoreactor with high efficiency was appropriate to degradation of the high concentration of 2,4-D solution (200 mg/L). After 5 successive cycles with 25 h of irradiation, P25 and P25/β-CD maintained as high 2,4-D removal efficiency as 82.6, 84% respectively, with excellent stability and reusability. ConclusionThe photodegradation method can be used as an effective and environmental friendly process in the degradation of organic compound.

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Computational investigation on the host–guest inclusion process of norfloxacin into β-cyclodextrin

et al. 2016

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A theoretical (1)H NMR spectroscopy and thermodynamic analysis of the host-guest inclusion process involving the norfloxacin (NFX) into β-cyclodextrin (β-CD) was carried out. DFT structure and stabilization energies were obtained in both gas and aqueous phases. We could establish that the complex formation is enthalpy driven, and the hydrogen bonds established between NFX and β-CD play a major role in the complex stabilization. Besides, a theoretical (1)H NMR analysis has shown to be a supplementary proceeding to predict appropriately the inclusion mode of norfloxacin molecule into the β-CD. In this work, a theoretical study of the NFX@β-CD complex is reported for the first time, seeking a deep understanding of topology and thermodynamics of the inclusion complex formation. Graphical Abstract Topology, thermodynamic and (1)H NMR analysis of NFX@β-CD host-guest complexes.

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Stability and spatial arrangement of the 2,4-dichlorophenoxyacetic acid and β-cyclodextrin inclusion compound: A theoretical study

Cited by 13 publications

References 27 publications

Structure, stability, and dynamics of the inclusion complexes formed by auranofin derivatives and hydroxypropyl-β-cyclodextrin

Structure, stability, and dynamics of the inclusion complexes formed by auranofin derivatives and hydroxypropyl-β-cyclodextrin

Study of visible-light photocatalytic degradation of 2,4-dichlorophenoxy acetic acid in batch and circulated-mode photoreactors

Computational investigation on the host–guest inclusion process of norfloxacin into β-cyclodextrin

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