Thermodynamics of solubility, sublimation and solvation processes of parabens

Perlovich, German L.; Rodionov, Sergey; Bauer‐Brandl, Annette

doi:10.1016/j.ejps.2004.09.007

Cited by 57 publications

(45 citation statements)

References 31 publications

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“…The present work is a continuation of previous studies on thermodynamics of solvation of drug molecules (1)(2)(3)(4)(5)(6). Here, 2-acetaminophen and 3-acetaminophen molecules ( Fig.…”

Section: Introductionmentioning

confidence: 51%

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Influence of Position and Size of Substituents on the Mechanism of Partitioning: A Thermodynamic Study on Acetaminophens, Hydroxybenzoic Acids, and Parabens

et al. 2008

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Abstract. The objective of the present investigation was to study the influence of size, nature, and topology of substituents on the thermodynamic characteristics of sublimation, fusion, solubility, solvation, and partitioning processes of some drug and druglike molecules. Thermodynamic functions of sublimation process 2-acetaminophen and 3-acetaminophen were obtained on the basis of temperature dependencies of vapor pressure by the transpiration method. Thermodynamic characteristics of solubility processes in water, n-octanol, and n-hexane were calculated from the temperature dependencies of solubility using the solubility saturation method. For evaluation of fusion parameters, differential scanning calorimetry was used. A new approach to distinguishing specific and nonspecific energetic terms in the crystal lattice was developed. Specific and nonspecific solvation terms were distinguished using the transfer from the "inert" n-hexane to the other solvents. For the acetaminophen compounds and for some related drug molecules, the correlation between melting points and a parameter describing the ratio between specific and nonspecific interaction in the crystal lattices was obtained. A diagram enabling analysis of the mechanism of the partitioning process was applied. It was found that for isomers of benzoic acids and for acetaminophens, the position of substituents affects the mechanism of the partitioning process but not the extent of partitioning ($G 0 tr values). In contrast to this, an increased size of substituents (parabens) leads to essential changes in $G 0 tr values, but the mechanism of the partitioning process stays the same.

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“…The present work is a continuation of previous studies on thermodynamics of solvation of drug molecules (1)(2)(3)(4)(5)(6). Here, 2-acetaminophen and 3-acetaminophen molecules ( Fig.…”

Section: Introductionmentioning

confidence: 51%

“…It is interesting to analyze differences in the ratio between specific and nonspecific interactions in the crystals (e sub ¼ $H nonÀspec sub $H spec sub ) and in solutions (ɛ H ) for the compounds studied together with the hydroxybenzoic acid isomers (5) and parabens (2). The experimental data of the (Fig.…”

Section: -Acetaminophen 3-acetaminophenmentioning

confidence: 99%

Influence of Position and Size of Substituents on the Mechanism of Partitioning: A Thermodynamic Study on Acetaminophens, Hydroxybenzoic Acids, and Parabens

et al. 2008

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“…The final cluster of amide-like compounds consists in (22)(23)(24)(25)(26). All are 'unknowns,' but certain trends can be anticipated.…”

Section: Results Returned To Participantsmentioning

confidence: 99%

The SAMPL2 blind prediction challenge: introduction and overview

Geballe¹,

Skillman²,

Nicholls³

et al. 2010

J Comput Aided Mol Des

208

240

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The interactions between a molecule and the aqueous environment underpin any process that occurs in solution, from simple chemical reactions to protein-ligand binding to protein aggregation. Fundamental measures of the interaction between molecule and aqueous phase, such as the transfer energy between gas phase and water or the energetic difference between two tautomers of a molecule in solution, remain nontrivial to predict accurately using current computational methods. SAMPL2 represents the third annual blind prediction of transfer energies, and the first time tautomer ratios were included in the challenge. Over 60 sets of predictions were submitted, and each participant also attempted to estimate the error in their predictions, a task that proved difficult for most. The results of this blind assessment of the state of the field for transfer energy and tautomer ratio prediction both indicate where the field is performing well and point out flaws in current methods.

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“…Therefore, this parameter is used to determine the specific packing of solid state crystalline substances [3]. As a consequence of such capability, sublimation enthalpy is used to describe the solvation of molecules, particularly drug molecules [4][5][6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

A group contribution model for determining the sublimation enthalpy of organic compounds at the standard reference temperature of 298K

Gharagheizi

Ilani-Kashkouli

Acree

et al. 2013

Fluid Phase Equilibria

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This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Abstract  The sublimation enthalpy provides a measure of molecular interactions in the solid phase. Practical applications involving sublimation enthalpies include the estimation of the crystal lattice energy of molecular crystals, estimation of the enthalpy of solvation of crystalline organic compounds, and prediction of the environmental fate and vapor pressures of solid compounds. Recently an extensive compilation of phase change enthalpies, including sublimation enthalpies of pure organic and organometallic compounds, was published [1]. This collection of sublimation enthalpies for 1269 compounds at the standard temperature of 298.15 K was used in this study for the development of a predictive model. The compounds in the collection are composed of carbon, hydrogen, nitrogen, oxygen, phosphorous, sulfur, fluorine, chlorine, bromine, and iodine. This paper presents a reliable group contribution model for the estimation of the sublimation enthalpies of organic compounds. The group contribution model developed is able to predict the standard molar enthalpies of sublimation to within an average absolute relative deviation of 6.4%, which is of sufficient accuracy for many practical applications.

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Thermodynamics of solubility, sublimation and solvation processes of parabens

Cited by 57 publications

References 31 publications

Influence of Position and Size of Substituents on the Mechanism of Partitioning: A Thermodynamic Study on Acetaminophens, Hydroxybenzoic Acids, and Parabens

Influence of Position and Size of Substituents on the Mechanism of Partitioning: A Thermodynamic Study on Acetaminophens, Hydroxybenzoic Acids, and Parabens

The SAMPL2 blind prediction challenge: introduction and overview

A group contribution model for determining the sublimation enthalpy of organic compounds at the standard reference temperature of 298K

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