Thermodynamic evidence for nano-heterogeneity in solutions of the macrocycle C-butylresorcin[4]arene in non-aqueous solvents

Riveros, Diana C.; Hefter, Glenn; Vargas, Édgar F.

doi:10.1016/j.jct.2018.06.006

Cited by 5 publications

(2 citation statements)

References 24 publications

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“…Figure 4 shows that in the case of 2-HP-β-CD, ∘ increase with the concentration (BV > 0) at the temperature of 298.15 K, but it decreases (BV < 0) with the concentration at 310.15 K; on the contrary, Figure 5 shows that for 2-HP-γ-CD, ∘ increase with the concentration (BV > 0) at the two temperatures studied. Positive values of BV have been related to destructive overlap in solvation cells of solute (decreased degree of solvent structuring) and negative values have been related to cooperative overlap (increased degree of solvent structuring) [32]. The BV values found for these solutes suggest a decrease in the degree of structuring of the solvent for 2-HPγ-CD, independent of the temperature, while for 2-HP-β-CD the increase in temperature causes that the decreasing effect observed at 298.15 K to change until it becomes an increase in the degree of structuring of the solvent when the temperature rises up to 310.15 K. The standard partial molar volume value found for 2-HP-β-CD is in good agreement with those reported by other authors [11,31].…”

Section: Binary Systems: Cyclodextrin + Watermentioning

confidence: 99%

New Contributions to the Study of the Interaction between Hydrocortisone and Hydroxypropyl-Cyclodextrins in Aqueous Solution

Maldonado,

Sanabria,

Romero

et al. 2024

Preprint

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In the present work, the interactions between hydrocortisone and cyclodextrins were investigated. The cyclodextrins selected for this study were hydroxypropyl-α-cyclodextrin, hydroxypropyl-β-cyclodextrin and hydroxypropyl-γ-cyclodextrin. The study was carried out using density measurements, 1H-NMR and FT-IR spectroscopy. Preliminary studies show that hydroxypropyl-α-cyclodextrin has a low affinity for hydrocortisone, while hydroxypropyl-β-cyclodextrin and hydroxypropyl-γ-cyclodextrin have a good affinity for hydrocortisone in both solid state and solution. The study was carried out at two temperatures: 298.15 K and 310.15 K. The results suggest that at both temperatures, the system 2-HP-β-CD + HC induces an increase in the solvent structure, with increasing the solute concentration in the solution, while on the contrary the system 2-HP-γ-CD + HC induces a decrease in the solvent structure when the concentration of the solute in the system increases.

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Section: Binary Systems: Cyclodextrin + Watermentioning

confidence: 99%

New Contributions to the Study of the Interaction between Hydrocortisone and Hydroxypropyl-Cyclodextrins in Aqueous Solution

Maldonado,

Sanabria,

Romero

et al. 2024

Preprint

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“…While some physicochemical properties of C -ARAs have been reported, − rather little is known about their enthalpies of solution (Δ sln H ) in either aqueous or nonaqueous solvents. , Such properties are not only of intrinsic interest but can also provide fundamental insight into the behavior of C -ARAs in solution and, by analogy, of other classes of macrocyclic compounds. However, apart from the previous work by our group, , to the best of our knowledge there are no thermodynamic data on related systems from which worthwhile conclusions can be drawn at the present time.…”

Section: Introductionmentioning

confidence: 99%

Enthalpies of Solution of C-Alkylresorcin[4]arenes in Water and Acetonitrile: Hydrophilic and Hydrophobic Effects

2019

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Enthalpies of solution, Δ sln H, of six Calkylresorcin[4]arene (C-ARA) solids, with alkyl substituents varying systematically from methyl (Me) to hexyl (Hx), have been measured in water, using solubility data, and in acetonitrile, by direct calorimetry. For all of the C-ARAs studied, the values of Δ sln H were highly favorable (exothermic) for dissolution into water but were strongly unfavorable (endothermic) for dissolution into acetonitrile (ACN). The differences between the two solvents varied systematically with increasing carbon chain length, from about 100 kJ•mol −1 (for Me) to 140 kJ•mol −1 (for Hx). These extraordinary variances can be attributed to the loss of hydrophilic hydration of the eight −OH groups on the rim of the C-ARAs and also by the loss of (enthalpically favorable) hydrophobic hydration of the alkyl chains upon transfer from the highly structured, strongly Hbonding water to the aprotic, relatively weak donor/acceptor ACN. Although Δ sln H values for the present C-ARAs in H 2 O are strongly favorable, they are more than counteracted by even larger negative changes in the entropy of dissolution, Δ sln S. This enthalpy/entropy compensation effect is consistent with the low aqueous solubilities (<10 −3 mol•kg −1 ) of the C-ARAs and their slight increase with increasing carbon chain length, which is opposite to typical behavior of the homologous series of organic molecules.

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Temperature effect on the solvation of two ionic resorcin[4]arenes from volumetric and acoustic properties in polar media

Moreno-Gómez

Buchner

Vargas

2019

Journal of Molecular Liquids

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Thermodynamic evidence for nano-heterogeneity in solutions of the macrocycle C-butylresorcin[4]arene in non-aqueous solvents

Cited by 5 publications

References 24 publications

New Contributions to the Study of the Interaction between Hydrocortisone and Hydroxypropyl-Cyclodextrins in Aqueous Solution

New Contributions to the Study of the Interaction between Hydrocortisone and Hydroxypropyl-Cyclodextrins in Aqueous Solution

Enthalpies of Solution of C-Alkylresorcin[4]arenes in Water and Acetonitrile: Hydrophilic and Hydrophobic Effects

Temperature effect on the solvation of two ionic resorcin[4]arenes from volumetric and acoustic properties in polar media

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