Equilibrium solubility, preferential solvation and solvent effect study of clotrimazole in several aqueous co-solvent solutions

Li, Yanxun; Li, Congcong; Gao, Xuejin; Lv, Hekun

doi:10.1016/j.jct.2020.106255

Cited by 13 publications

(15 citation statements)

References 42 publications

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“…The XRD patterns of clotrimazole crystals recovered from the solvents are presented in Figure . Strong characteristic diffraction peaks at 2θ values of 9.28°, 9.92°, 12.56°, 16.86°, 18.80°, 19.68°, and 20.94° can be observed, which are the same as those reported in the literature . These results show that clotrimazole does not have a polymorph.…”

Section: Resultssupporting

confidence: 87%

“…The amount of dissolved clotrimazole in the solutions was determined using high-performance liquid chromatography. The comparison between the solubility measured in this work and that reported by Li et al is presented in Table . For n -propanol, the solubility values by Li et al from 280.15 to 303.15 K are consistent with our results.…”

Section: Resultsmentioning

confidence: 54%

“…The comparison between the solubility measured in this work and that reported by Li et al is presented in Table . For n -propanol, the solubility values by Li et al from 280.15 to 303.15 K are consistent with our results. However, when the temperature is above 308.15 K, their values are noticeably lower than ours.…”

Section: Resultsmentioning

confidence: 54%

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Solubility and Thermodynamic Properties of Clotrimazole in 16 Organic Solvents at Temperature of 283.15 to 323.15 K

Wang

Yang

et al. 2023

J. Chem. Eng. Data

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In this paper, the solubility of clotrimazole, an antifungal drug, in 10 alcohols (n-propanol, iso-propanol, n-butanol, iso-butanol, sec-butanol, n-pentanol, iso-pentanol, n-hexanol, n-heptanol, and n-octanol) and 6 esters (methyl acetate, ethyl acetate, npropyl acetate, n-butyl acetate, isopropyl acetate, and methyl propionate) was experimentally determined using a laser dynamic solubility-monitoring device in a temperature range of 283.15 to 323.15 K at atmospheric pressure. The functions of solubility versus temperature were regressed using three semi-empirical models (modified Apelblat, three-parameter van't Hoff, and λh) and two activity coefficient models (Wilson and NRTL). The results show that all the five models can be used to correlate the solubility of clotrimazole with temperature in these solvents satisfactorily. Furthermore, the thermodynamic mixing properties (Δ mix G, Δ mix H, Δ mix S, ln(γ 1 ∞ ), and H 1 E, ∞ ) were evaluated using the measured solubility values and Wilson model parameters.

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Section: Resultssupporting

confidence: 87%

Section: Resultsmentioning

confidence: 54%

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Solubility and Thermodynamic Properties of Clotrimazole in 16 Organic Solvents at Temperature of 283.15 to 323.15 K

Wang

Yang

et al. 2023

J. Chem. Eng. Data

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“…The triarylmethyl moiety is a sterically hindered and nonpolar motif, creating a large hydrophobic/nonpolar pocket within the molecule that results in extremely low aqueous solubility. 21 This ideally positions Clotrimazole-inspired ILs to possess a desired balance between biocompatibility and solubility. In light of these considerations, the development of ILs containing various triarylmethyl moieties emerges as a significant strategy for widening the catalog of available ILs, while also establishing key structural diversity rubrics for cation design.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Anticancer Agents as Design Archetypes: Insights into the Structure–Property Relationships of Ionic Liquids with a Triarylmethyl Moiety

et al. 2022

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A fundamental challenge underlying the design principles of ionic liquids (ILs) entails a lack of understanding into how tailored properties arise from the molecular framework of the constituent ions. Herein, we present detailed analyses of novel functional ILs containing a triarylmethyl (trityl) motif. Combining an empirically driven molecular design, thermophysical analysis, X-ray crystallography, and computational modeling, we achieved an in-depth understanding of structure–property relationships, establishing a coherent correlation with distinct trends between the thermophysical properties and functional diversity of the compound library. We observe a coherent relationship between melting (T m) and glass transition (T g) temperatures and the location and type of chemical modification of the cation. Furthermore, there is an inverse correlation between the simulated dipole moment and the T m/T g of the salts. Specifically, chlorination of the ILs both reduces and reorients the dipole moment, a key property controlling intermolecular interactions, thus allowing for control over T m/T g values. The observed trends are particularly apparent when comparing the phase transitions and dipole moments, allowing for the development of predictive models. Ultimately, trends in structural features and characterized properties align with established studies in physicochemical relationships for ILs, underpinning the formation and stability of these new lipophilic, low-melting salts.

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Equations for the Correlation and Prediction of Partition Coefficients of Neutral Molecules and Ionic Species in the Water–Isopropanol Solvent System

et al. 2021

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We use literature data on solubilities of 46 compounds in the water-isopropanol (IPA) system to obtain the corresponding partition coefficients, P, for transfer from water to water-IPA mixtures. We have then used our previously constructed linear free energy equation to obtain equations that correlate log 10 P at water-IPA intervals across the entire water-IPA system. These equations can then be used to predict partition coefficients and solubilities of further compounds in the water-IPA systems at 298 K. The coefficients in our linear free energy equation encode information on the physicochemical properties of the water-IPA mixtures. We show that the hydrogen bond basicity of the water-IPA mixtures only increases slightly from water to IPA, but that the hydrogen bond acidity of the mixtures decreases markedly from water to IPA in a smooth continuous manner.We have also used data on ions and on ionic species to set out equations for the estimation of their partition coefficients from water to water-IPA mixtures. We find that for partition from water to IPA itself, log 10 P= -1.

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Equilibrium solubility, preferential solvation and solvent effect study of clotrimazole in several aqueous co-solvent solutions

Cited by 13 publications

References 42 publications

Solubility and Thermodynamic Properties of Clotrimazole in 16 Organic Solvents at Temperature of 283.15 to 323.15 K

Solubility and Thermodynamic Properties of Clotrimazole in 16 Organic Solvents at Temperature of 283.15 to 323.15 K

Anticancer Agents as Design Archetypes: Insights into the Structure–Property Relationships of Ionic Liquids with a Triarylmethyl Moiety

Equations for the Correlation and Prediction of Partition Coefficients of Neutral Molecules and Ionic Species in the Water–Isopropanol Solvent System

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