Thermodynamic aspects of solubility, solvation and partitioning processes of some sulfonamides

Perlovich, German L.; Ryzhakov, Alex M.; Strakhova, Nadezda N.; Kazachenko, Vladimir P.; Schaper, Klaus‐Jürgen; Raevsky, Oleg A.

doi:10.1016/j.jct.2010.12.007

Cited by 10 publications

(4 citation statements)

References 23 publications

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“…Our previous works − studied the structures, packing architecture, topology of hydrogen bond networks, sublimation, solubility, and solvation characteristics of 14 sulfonamides ( I – XIV ). As a continuation of the study, this work focuses on the comparative analysis of the published compounds with new ones: N -(2-nitrophenyl)-benzene-sulfonamide ( XV ), N -(2,5-dibromophenyl)-benzene-sulfonamide ( XVI ), 4-amino- N -(2-bromo-4-nitrophenyl)-benzene-sulfonamide ( XVII ), 4-amino- N -(3-chloro-4-methylphenyl)-benzene-sulfonamide ( XVIII ), 4-amino- N -(2-methoxy-3-chlorphenyl)-benzene-sulfonamide ( XIX ), N -(2-chloro-3-pyridinyl)-benzene-sulfonamide ( XX ), 4-nitro- N -(5-methyl-2-pyridinyl)-benzene-sulfonamide ( XXI ), 4-amino- N -(3-methoxypyrazinyl)-benzene-sulfonamide ( XXII ), 4-amino-N-(3,4-dimethyl-5-isoxazolyl)-benzene-sulfonamide ( XXIII ), and 4-amino- N -(5-methyl-3-isoxazolyl)-benzene-sulfonamide ( XXIV ) (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Sulfonamide Molecular Crystals: Structure, Sublimation Thermodynamic Characteristics, Molecular Packing, Hydrogen Bonds Networks

Perlovich

Ryzhakov

Ткачев

et al. 2013

Crystal Growth & Design

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The crystal structures of ten sulfonamides have been determined by X-ray diffraction. On the basis of our previous data, the obtained results and literature data crystal properties including molecular conformational states, packing architecture, and hydrogen bond networks were comparatively analyzed using graph set notations. Conformational flexibility of the bridge connecting two phenyl rings was studied. It was found out that the most frequently occurring graphs for compounds with a single hydrogen bond are infinite chains with four atoms included. The molecular packing architecture of the selected crystals may be conditionally divided into three different groups. The idea underlying such classification is the difference in structure and composition of molecular layers that can be singled out for most packings. The influence of various molecular fragments on crystal lattice energy was analyzed. A correlation between melting points and fragmental molecular interactions in the crystal lattices was obtained. The thermodynamic aspects of the sulfonamide sublimation were studied by determining the temperature dependence of vapor pressure using the transpiration method. A correlation between the Gibbs energy of the sublimation process and the melting points was found. Besides, a regression equation was derived to describe the correlation between the sublimation entropy terms and crystal density data calculated from X-ray diffraction results.

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Section: Introductionmentioning

confidence: 99%

Sulfonamide Molecular Crystals: Structure, Sublimation Thermodynamic Characteristics, Molecular Packing, Hydrogen Bonds Networks

Perlovich

Ryzhakov

Ткачев

et al. 2013

Crystal Growth & Design

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“… a Relative standard uncertainty for solubility values u r ( X 2 298 ) = 0.03. b Reference . c Reference . d Reference . e Reference . f Reference . g Reference . h Calculated by ACD, ref . i Reference . j Experimental p K a listed by ACD, ref . k Reference . …”

Section: Resultsmentioning

confidence: 99%

Impact of Sulfonamide Structure on Solubility and Transfer Processes in Biologically Relevant Solvents

et al. 2014

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Solubility values of 39 sulfonamides in water, 1-octanol, and 1-hexane were determined by the isothermal saturation method. Thermophysical characteristics of fusion processes (melting points and fusion enthalpies) of the selected substances were measured by the DSC method. The impact of molecule structural modification on solubility processes in the solvents was analyzed. Transfer processes from water to 1-octanol, water to 1-hexane, and 1-hexane to 1-octanol were studied. Correlation equations connecting Gibbs energies of the solubility and the transfer processes with physicochemical descriptors and thermophysical characteristics were obtained.

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“…A diagram method applied by us earlier was used to match entropy and enthalpy terms of dissolution. The diagram portrayed in Figure highlights contributions of thermodynamic functions in the process of dissolution of the compounds under study.…”

Section: Resultsmentioning

confidence: 99%

“…The present paper is a continuation of the investigation we undertook to study the solubility and partitioning of drug and drug-like compounds in biological media. , The effects of chemical nature and structure of new spiro-compound derivatives on their solubility in model biological media (hexane and a buffer with pH 7.4) have been studied in the present paper. The choice of the solvents was dictated by the fact that hexane and the buffer are a model pair of solvents that imitate the properties of a blood–brain barrier. , The examination of the properties of the molecules in these media gives insight into the processes of passive transport through organism membranes and allows imparting the desired design to bioavailable drug molecules.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamics of Solubility Processes of Novel Drug-like Spiro-Derivatives in Model Biological Solutions

et al. 2012

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The solubility of 11 new drug-like spiro-compounds in buffer solution (pH 7.4) and hexane was measured by the isothermal saturation technique in the temperature range of (293 to 315) K. The influence of substituent chemical nature, branching of aliphatic chain, and inclusion of oxygen and halogen atoms in molecule structure were investigated. The correlation dependences of the solubility on molecular descriptors and thermophysical properties were estimated. Standard thermodynamic solubility functions for the test compounds were calculated. The conclusion reveals the dominant contribution of dispersion forces in the solution process.

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Thermodynamic aspects of solubility, solvation and partitioning processes of some sulfonamides

Cited by 10 publications

References 23 publications

Sulfonamide Molecular Crystals: Structure, Sublimation Thermodynamic Characteristics, Molecular Packing, Hydrogen Bonds Networks

Sulfonamide Molecular Crystals: Structure, Sublimation Thermodynamic Characteristics, Molecular Packing, Hydrogen Bonds Networks

Impact of Sulfonamide Structure on Solubility and Transfer Processes in Biologically Relevant Solvents

Thermodynamics of Solubility Processes of Novel Drug-like Spiro-Derivatives in Model Biological Solutions

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