Solubility of<scp>dl</scp>-serine and<scp>dl</scp>-phenylalanine in aqueous mixtures of dimethyl sulfoxide and solvation thermodynamics

Hossain, Aslam; Roy, Sanϳay; Ghosh, Srabani; Mondal, Samiran; Dolui, Bijoy Krishna

doi:10.1039/c5ra12403d

Cited by 48 publications

(34 citation statements)

References 33 publications

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“…It is noteworthy that the co-solvent DMSO is an important polar aprotic solvent with very low toxic and immense biological importance. 6 It dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. In the following step, the effect of temperature on the solubility of naringin in the binary aqueous mixtures is analyzed to evaluate the thermodynamic quantities involved in the process of solubility.…”

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Solubility temperature and solvent dependence and preferential solvation of citrus flavonoid naringin in aqueous DMSO mixtures: an experimental and molecular dynamics simulation study

et al. 2017

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This study describes the thermodynamics of dissolution of flavonoid naringin in different aqueous solutions of dimethyl sulfoxide (DMSO) containing 0-100% (w/w) under atmospheric pressure and over a temperature range of 298.15 to 325.15 K. The temperature dependence of solubility of naringin was analyzed using the modified Apelblat equation model, ideal model, and the lH equation model. In a mean harmonic temperature, the dissolution thermodynamic parameters of naringin containing DG sol , DH sol and DS sol were also calculated. Furthermore, the effects of solvent composition on the solubility of this flavonoid were analyzed in terms of Hildebrand's solubility parameter (d H ) and Kamlet, Abboud and Taft (KAT) solvatochromic parameters (a, b, and p*). Finally, the preferential solvation parameters of the flavonoid naringin by DMSO (dx DMSO,S ) were determined from experimental solubility data using the inverse Kirkwood-Buff integrals (IKBIs). It was found that water preferentially solvates naringin in waterrich mixtures while DMSO forms local solvation shells in compositions from 50% (w/w) or x DMSO ¼ 0.19 up to pure co-solvent. Moreover, the structure of solvation shells of naringin in the under study mixtures was obtained by molecular dynamics (MD) simulations. The computational results showed that in the compositions x DMSO > 0.20, the probability of presence of the DMSO molecules in vicinity of naringin is more than water molecules. These findings are compatible with the available IKBI data.

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“…5,6 Furthermore, the solubility data of solutes in different solvents are necessary for determining the appropriate solvents for extraction, separation, production, and purication of organic compounds.…”

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Solubility temperature and solvent dependence and preferential solvation of citrus flavonoid naringin in aqueous DMSO mixtures: an experimental and molecular dynamics simulation study

et al. 2017

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“…Moreover, our main concern in the current study is to determine and characterize the total transfer Gibbs energy (DG 0 t ðiÞ) in such binary solvent mixtures; therefore, we also have assumed here that the contribution of activity coefficient is negligible [11,12,15,17,[19][20][21][22][23][24]44]. DG 0 t ðiÞ is also related as DG 0 t ðiÞ ¼ DG 0 s ðiÞ À DG 0 R ðiÞ, where DG 0 t ðiÞ, DG 0 s ðiÞ and DG 0 R ðiÞ are the Gibbs energies of the amino acid solutions in co-solvent (aqueous ME) and reference solvent, water, respectively.…”

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confidence: 99%

“…There are several methods [38][39][40][41][42][43] for the determination of the activity coefficients that involve various theoretical aspects and assumptions. But for simplicity, in many earlier studies the activity coefficient was assumed to be unity [11,12,15,17,[19][20][21][22][23][24]44] during the determination of the Gibbs energy of several amino acids in solution.…”

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confidence: 99%

Chemical Transfer Energetics of a Series of Homologous α-Amino Acids in Quasi-Aprotic 2-Methoxyethanol–Water Mixtures

2016

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The zwitterionic solvation behavior of a series of the homologous a-amino acids glycine (Gly), DL-alanine (Ala), DL-a-amino butyric acids (Aba) and DL-nor-valine (Val), in water and in aqueous mixtures of 2-methoxyethanol, have been studied at equidistant temperature intervals in the range of 288.15-308.15 K, using the solubility method. The solubility data were analyzed according to the 'formol titrimetric' process. Standard Gibbs energies DG 0 t ðiÞ and entropies DS 0 t ðiÞ of transfer were calculated and are discussed. The observed DG 0 t ðiÞ and TDS 0 t ðiÞ versus composition profiles are complicated because of the various interaction effects. The chemical effects of the transfer Gibbs energies DG 0 t;ch ðiÞ and entropies of transfer TDS 0 t;ch ðiÞ have been obtained after elimination of the cavity effect, estimated by the scaled particle theory and dipole-dipole interaction effects, calculated by use of the Keesom orientation expression. The chemical contributions to transfer energetics of homologous a-amino acids are guided by the combined effects of increased dispersion interaction, basicity and decreased acidity, hydrogen bonding effects and hydrophilic hydration of aqueous 2-methoxy ethanol as compared to that of reference solvent, water. In this context the solvating characters of protic ethylene glycol are also referred to for comparison.

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“…There should be no difference in the log P values for l -phenylalanine and dl -phenylalanine for transfer to a given solvent. Also included in Table 13 are recent determinations of solubilities and hence log P values in dimethylsulfoxide, 61 methanol, 62 and ethanol. 63 Where necessary, we have averaged the various values.…”

Section: Resultsmentioning

confidence: 99%

Solvation Descriptors for Zwitterionic α-Aminoacids; Estimation of Water–Solvent Partition Coefficients, Solubilities, and Hydrogen-Bond Acidity and Hydrogen-Bond Basicity

Abraham

Acree

2019

ACS Omega

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The literature data on solubilities and water–solvent partition coefficients have been used to obtain properties or “Absolv descriptors” for zwitterionic α-aminoacids: glycine, α-alanine (α-aminopropanoic acid), α-aminobutanoic acid, norvaline (α-aminopentanoic acid), norleucine (α-aminohexanoic acid), valine (α-amino-3-methylbutanoic acid), leucine (α-amino-4-methylpentanoic acid), and α-phenylalanine. Together with equations that we have previously constructed, these descriptors can be used to estimate further solubilities and partition coefficients in a variety of organic solvents and in water–methanol and water–ethanol mixtures. It is shown that equations for neutral solutes are inadequate for the description of solubilities and partition coefficients for these α-aminoacids, and our equations developed for use with both neutral and ionic solutes must be used. The Absolv descriptors include those for hydrogen-bond acidity, A , and hydrogen-bond basicity, B . We find that both of these descriptors are far smaller in value than those for compounds that contain the corresponding ionic groups. Thus, A for α-alanine is 0.28, but A for the ethylammonium cation is 1.31; B for α-alanine is 0.83, and yet B for the acetate anion is no less than 2.93. The additional descriptors that we developed for equations that involve ions, J + and J – , are very significant for the α-aminoacids, although numerically smaller than for ionic species such as EtNH 3 + and CH 3 CO 2 – .

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Solubility ofdl-serine anddl-phenylalanine in aqueous mixtures of dimethyl sulfoxide and solvation thermodynamics

Abstract: Solvation thermodynamic data of dl-serine and dl-phenylalanine in aqueous mixtures of dimethylsulfoxide at 298.15 K were determined from solubility measurement.

Cited by 48 publications

References 33 publications

Solubility temperature and solvent dependence and preferential solvation of citrus flavonoid naringin in aqueous DMSO mixtures: an experimental and molecular dynamics simulation study

Solubility temperature and solvent dependence and preferential solvation of citrus flavonoid naringin in aqueous DMSO mixtures: an experimental and molecular dynamics simulation study

Chemical Transfer Energetics of a Series of Homologous α-Amino Acids in Quasi-Aprotic 2-Methoxyethanol–Water Mixtures

Solvation Descriptors for Zwitterionic α-Aminoacids; Estimation of Water–Solvent Partition Coefficients, Solubilities, and Hydrogen-Bond Acidity and Hydrogen-Bond Basicity

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