Excess Molar Refraction Research Articles

Investigation of the retention behavior of structurally diverse drugs on alpha1 acid glycoprotein column: Insight on the molecular factors involved and correlation with protein binding data

Retention of 49 structurally diverse drugs on alpha1 acid glycoprotein column was investigated under different chromatographic conditions. Acetonitrile and 2-propanol were used as organic modifiers at different percentages and the pH was adjusted at 7.0 using PBS. Analysis of extrapolated and isocratic retention in terms of lipophilicity and electrostatic interactions revealed significant effect of the nature and percentage of organic modifier, which was attributed to the different shielding degree of the charged sites on the stationary phase by the buffer constituents. AGP retention factors were compared to HSA retention factors analyzed previously. Application of LSER analysis, extended to incorporate fractions ionized, demonstrated hydrogen bond acidity, dipolarity/polarizability and excess molar refraction as the most significant parameters for all AGP chromatographic indices, elucidating the differentiation of AGP retention from octanol–water partitioning and HSA retention. An attempt to correlate AGP chromatographic indices to AGP association constants, available in literature, supported the importance of stationary shielding in retention mechanism. Thus, isocratic retention factors logk10(ACN)AGP show a moderate but still better performance than lipophilicity in the case of A variant and may be a useful tool for the estimation of relevant association constants. For F1/S binding simulation lower stationary phase shielding is needed to obtain a significant two term regression equation, where logk20(ACN)AGP exerts a secondary contribution next to the most important bulk effect expressed by molecular weight.

Volumetric and optical properties for some (2-butanone + chloroalkane) binary mixtures at T = 298.15 K

Densities and refractive indices data for five binary systems of 2-butanone+1-chloropentane, + 1,3-dichloropropane, + 1,4-dichlorobutane, + 1,1,1-trichloroethane, + 1,1,2,2-tetrachloroethane were measured at T=298.15K and atmospheric pressure, over the entire mole fraction range. The densities data of the studied mixtures have been used to calculate the excess molar volumes and the partial volumetric properties at infinite dilution. The refractive index data were used to calculate excess molar refractions and the deviations of experimental refraction indices from the predicted results were compared with those calculated using several mixing rules (Lorentz–Lorenz, Gladstone–Dale, Arago–Biot, Edwards, Eykman). The excess quantities were fitted to a Redlich–Kister type polynomial equation to derive the binary coefficients and estimate the standard deviations between the experimental and calculated quantities. The excess molar volumes and the excess molar refraction have evidenced intermolecular interactions between the components of mixtures.

Prediction of formulation effects on dermal absorption of topically applied ectoparasiticides dosed in vitro on canine and porcine skin using a mixture‐adjusted quantitative structure permeability relationship

Topical application of ectoparasiticides for flea and tick control is a major focus for product development in animal health. The objective of this work was to develop a quantitative structure permeability relationship (QSPeR) model sensitive to formulation effects for predicting absorption and skin deposition of five topically applied drugs administered in six vehicle combinations to porcine and canine skin in vitro. Saturated solutions (20μL) of (14) C-labeled demiditraz, fipronil, permethrin, imidacloprid, or sisapronil were administered in single or binary (50:50 v/v) combinations of water, ethanol, and transcutol (6 formulations, n=4-5 replicates per treatment) nonoccluded to 0.64cm(2) disks of dermatomed pig or dog skin mounted in flow-through diffusion cells. Perfusate flux over 24h and skin deposition at termination were determined. Permeability (logKp), absorption, and penetration endpoints were modeled using a four-term Abrahams and Martin (hydrogen-bond donor acidity and basicity, dipolarity/polarizability, and excess molar refractivity) linear free energy QSPeR equation with a mixture factor added to compensate for formulation ingredient interactions. Goodness of fit was judged by r(2) , cross-validation coefficient, coefficients (q(2) s), and Williams Plot to visualize the applicability domain. Formulation composition was the primary determinant of permeation. Compounds generally penetrated dog skin better than porcine skin. The vast majority of permeated penetrant was deposited within the dosed skin relative to transdermal flux, an attribute for ectoparasiticides. The best QSPeR logKp model for pig skin permeation (r(2) = 0.86, q(2) s = 0.85) included log octanol/water partition coefficient as the mixture factor, while for dogs (r(2) = 0.91, q(2) s = 0.90), it was log water solubility. These studies clearly showed that the permeation of topical ectoparasiticides could be well predicted using QSPeR models that account for both the physical-chemical properties of the penetrant and formulation components.

Predicting Partition Coefficients of Polyfluorinated and Organosilicon Compounds using Polyparameter Linear Free Energy Relationships (PP-LFERs)

The environmental behavior, fate, and effects of polyfluorinated compounds (PFCs) and organosilicon compounds (OSCs) have received increasing attention in recent years. In this study, polyparameter linear free energy relationships (PP-LFERs) were evaluated for predicting partition coefficients of neutral PFCs and OSCs, using experimental data for fluorotelomer alcohols (FTOHs) and cyclic volatile methylsiloxanes (cVMS) reported in the literature and measured newly for this work. It was found that the recently proposed PP-LFER model that uses the McGowan characteristic volume (V), the logarithmic hexadecane-air partition coefficient (L), and three polar interaction descriptors can accurately describe partition coefficients of PFCs and OSCs. The prediction errors were <1 log unit when literature descriptors were used, and the errors were reduced to <0.2 log units on average by further optimization of the descriptors. Surprisingly, the conventional forms of PP-LFERs that include the excess molar refraction (E) sometimes led to substantial errors (>1 log unit) even with optimized parameters. The system parameters for octanol-water, air-water, octanol-air, oil-water, liposome-water, and organic carbon-water partition coefficients as well as the solute descriptors for FTOHs and cVMS were recalibrated in this work, which should provide even more reliable predictions of partition coefficients. The results also confirm the consistency of the published experimental partition coefficients for FTOHs and cVMS.

Densities, viscosities, refractive indices and excess properties of ortho- and meta-chloroaniline with 2-alkoxyethanols at 303.15 K

Densities (ρ), viscosities (η) and refractive indices (nD) were measured for the binary mixtures of o- and m-chloroaniline with 2-alkoxyethanols like 2-methoxyethanol, 2-ethoxyethanol and 2-butoxyethanol at 303.15K. From the experimental data, the values of excess molar volume (VE), deviation of viscosity (ηE), deviation of refractive index (ΔnD), excess molar refraction (RmE) and excess Gibbs free energy (ΔG⁎E) for the six binary mixtures were calculated and the values are fitted with Redlich–Kister polynomial equation. The values of all calculated parameters of the binary mixtures and their deviations indicate a strong specific type of interaction between the amino group (NH2) of chloroanilines with hydroxyl group (OH) of 2-alkoxyethanols.

Refractive Indices Measurement and Correlation for Selected Binary Systems of Various Polarities at 25 °C

New refractive indices at 25 °C were measured and are reported here for 19 binary mixtures of pentan-3-one+1,2-dichloroethane, +1,3-dichloropropane, +1,4-dichlorobutane, +trichloromethane, +1,1,1-trichloroethane, +1,1,2,2-tetrachloroethane; cyclopentanone+1-chlorobutane, +1,1,2,2-tetrachloroethane; cyclohexanone+1,1,2,2-tetrachloroethane; 5-chloro-2-pentanone+n-hexane, +toluene, +ethylbenzene; nitromethane+trichloromethane; and nitromethane or nitroethane, +1,2-dichloroethane, +1,3-dichloropropane, +1,4-dichlorobutane. The experimental refractive index deviations from linear mixing behavior have been evaluated and correlated consistently with the 3-parameter Redlich–Kister equation with good results. The molar refraction was also examined for the systems including pentan-3-one, cyclopentanone, cyclohexanone and 5-chloro-2-pentanone for which densities and excess molar volumes are available from previous works. Different theoretical (n, ρ) mixing rules were tested for these systems. The excess Gibbs energy G E and excess enthalpy H E values were considered together with the excess molar volumes V E, excess refractive indexes $$ n_{\text{D}}^{\text{E}} $$ , molar refraction R and excess molar refractions R E on mixing in the discussion of the influence of the alkyl chain length or of the nature of the second component in the mixture in terms of molecular interactions.

Structural determinants of drug partitioning in surrogates of phosphatidylcholine bilayer strata.

The knowledge of drug concentrations in bilayer headgroups, core, and at the interface between them is a prerequisite for quantitative modeling of drug interactions with many membrane-bound transporters, metabolizing enzymes and receptors, which have the binding sites located in the bilayer. This knowledge also helps understand the rates of trans-bilayer transport because balanced interactions of drugs with the bilayer strata lead to high rates, while excessive affinities for any stratum cause a slowdown. Experimental determination of bilayer location is so tedious and costly that the data are only available for some fifty compounds. To extrapolate these valuable results to more compounds at a higher throughput, surrogate phases have been used to obtain correlates of the drug affinities for individual strata. We introduced a novel system, consisting of a diacetyl phosphatidylcholine (DAcPC) solution with the water content of the fluid bilayer as the headgroup surrogate and n-hexadecane (C16) representing the core. The C16/DAcPC partition coefficients were measured for 113 selected compounds, containing structural fragments that are frequently occurring in approved drugs. The data were deconvoluted into the ClogP-based fragment solvation characteristics and processed using a solvatochromic correlation. Increased H-bond donor ability and excess molar refractivity of compounds promote solvation in the DAcPC phase as compared to bulk water, contrary to H-bond acceptor ability, dipolarity/polarizability, and volume. The results show that aromates have more balanced distribution in bilayer strata, and thus faster trans-bilayer transport, than similar alkanes. This observation is in accordance with the frequent occurrence of aromatic rings in approved drugs and with the role of rigidity of drug molecules in promoting intestinal absorption. Bilayer locations, predicted using the C16/DAcPC system, are in excellent agreement with available experimental data, in contrast to other surrogate systems.

In silico modelling for predicting the cationic hydrophobicity and cytotoxicity of ionic liquids towards the Leukemia rat cell line, Vibrio fischeri and Scenedesmus vacuolatus based on molecular interaction potentials of ions

In this study we present prediction models for estimating in silico the cationic hydrophobicity and the cytotoxicity (log [1/EC50]) of ionic liquids (ILs) towards the Leukemia rat cell line (IPC-81), the marine bacterium Vibrio fischeri and the limnic green algae Scenedesmus vacuolatus using linear free energy relationship (LFER) descriptors computed by COSMO calculations. The LFER descriptors used for the prediction model (i.e. excess molar refraction (E), dipolarity/polarizability (S), hydrogen-bonding acidity (A), hydrogen-bonding basicity (B) and McGowan volume (V)) were calculated using sub-descriptors (sig2, sig3, HBD3, HBA4, MR, and volume) derived from COSMO–RS, COSMO and OBPROP. With the combination of two solute descriptors (B, V) of the cation we were able to predict cationic hydrophobicity values (log ko ) with r 2 = 0.987 and standard error (SE) = 0.139 log units. By using the calculated log k o values, we were able to deduce a linear toxicity prediction model. In the second prediction study for the cytotoxicity of ILs, analysis of descriptor sensitivity helped us to determine that the McGowan volume (V) terms of the cation was the most important predictor of cytotoxicity and to simplify prediction models for cytotoxicity of ILs towards the IPC-81 (r 2 of 0.778, SE of 0.450 log units), Vibrio fischeri (r 2 of 0.762, SE of 0.529 log units) and Scenedesmus vacuolatus (r 2 of 0.776, SE of 0.825 log units). The robustness and predictivity of the two models for IPC-81 and Vibrio fischeri were checked by comparing the calculated SE and r 2 (coefficient of determination) values of the test set.

Studies on properties of ionic liquids 1-alkyl-3-methylimidazolium lactate at temperatures from (288.15 to 333.15) K

Two chiral ionic liquids based on lactic acid (LAILs), 1-ethyl-3-methylimidazolium lactate ([C2mim][Lact]) and 1-pentyl-3-methylimidazolium lactate ([C5mim][Lact]), have been prepared by the neutralization method and characterized by 1H NMR and DSC. Their density, surface tension and refractive index were measured at T {(288.15 to 333.15)±0.05}K. Since the LAILs can form strong hydrogen bonds with water, small amounts of water are difficult to remove by conventional methods. In order to eliminate the effect of the impurity as water, the standard addition method (SAM) was applied to these measurements. The molar volume of [Cnmim][Lact] (n=2,5), the thermal expansion coefficient, α, the surface excess entropy, Sa, the surface excess energy Ea, parachor, P, and molar refraction, Rm, were obtained. According to the methods of both Kabo and Rebelo, the molar enthalpy of evapouration of the LAILs was estimated using experimental values for the surface tension and molar volume. At the same time, the surface tension of the LAILs may be estimated using the data of the parachor and refractive index. The estimated values of the surface tension correlate quite well with the corresponding experimental values.

Densities and refractive indices for binary and ternary mixtures of (carbon tetrachloride + β-pinene + 2-chlorobutane) at T = 298.15 K

Densities and refractive indices of ternary mixtures of (carbon tetrachloride + β-pinene + 2-chlorobutane) and related binary mixtures (carbon tetrachloride + β-pinene), (carbon tetrachloride + 2-chlorobutane), and (β-pinene + 2-chlorobutane) have been measured over the whole composition range at T = 298.15 K for the liquid region and at ambient pressure. Excess molar volumes, partial molar volumes, excess partial molar volumes, partial molar volumes at infinite dilution, excess refractive index, and excess molar refractivity were calculated from experimental data and reported for the binary and ternary mixtures at T = 298.15 K. The excess functions were correlated with the Redlich-Kister and Cibulka equation for binary and ternary mixtures, respectively. Especially the ternary excess molar volumes were compared with the estimated values from the binary contribution model equations of Tsao-Smith, Jacob-Fitzer, Kohler, and Rastogi. The experimental results of constitute binary mixtures have been used to test the applicability of the Prigogine-Flory-Paterson theory.

Individual Ionic Surface Tension Increments in Aqueous Solutions

Surface tension increments by aqueous electrolytes, kE = [γ(cE) - γ(W)]/cE, can be split into the ionic values, ki (kE = Σνiki), on an arbitrary but plausible manner, notwithstanding the effects of counterions on the behavior of specific ions. Values for 41 ions, mono- and polyatomic and uni- and multivalent, are presented in conjunction with some other ionic properties. The surface potential increments of electrolytes, ΔΔχ = ΔχE (at cE = 1 M) - ΔχW, depend linearly on the kE values for four anion series with common cations and on the differences between cation and anion ki values. The ki (normalized to unit charge number) are correlated linearly with the ionic radii ri, the excess ionic molar refractivity over that of water, RDi - RDW, the ionic softness parameters (modified by adding +0.5 to anion and -0.5 to cation values), σ±0.5, and to the geometrical factor of water structure making/breaking, ΔHBG. No correlation takes place with the ionic polarization corrected for that of water, αi* = αi - αW(ri/rW)(3), nor with the molar Gibbs energy or enthalpy of hydration. The latter fact implies that ion dehydration does not play a major role in the sorption/desorption of ions at the surface. The correlations that were found are discussed in a qualitative manner and compared with theoretical arguments in the literature.

Modeling the effect of experimental variables on the in vitro permeation of six model compounds across porcine skin

A majority of quantitative structure-permeability relationships (QSPeRs) predict the permeability coefficient (k(p)) of compounds topically applied as infinite, saturated doses from water vehicles. Alternate delivery vehicles and other experimental variables are rarely incorporated in such models. This research presents the development and statistical validation of QSPeR models that incorporate the effects of penetrant, vehicle, and experimental conditions such as dose volume (finite/infinite), and saturation level (saturated/unsaturated). A composite parameter, a mixture factor (MF), was also included to account for the physicochemical properties of the compound/vehicle mixture components. The resultant models effectively described skin flux and absorption, identifying the summation of hydrogen bond acidity and basicity, excess molar refractivity, dose volume, saturation level, and vehicle as the most prominent factors influencing flux values. The main factors influencing absorption values were the summation of hydrogen bond basicity, dipolarity/polarizability, the McGowan characteristic volume, dose volume, saturation level, and vehicle. The same MF (inverse of the melting point) was considered suitable to describe both flux and absorption. For endpoints involving skin deposition, log propylene glycol solubility was a more suitable MF. Such models show potential for use in drug delivery and toxicology research, specifically in assessing percutaneous absorption data collected under different experimental conditions.

A Correlation for 1,9-Decadiene/Water Partition Coefficients

An important series of papers by Xiang, Anderson, and coworkers has established the strong correlation between phospholipid bilayer membrane permeability and the 1,9-decadiene/water partition coefficient over a wide range of compounds, elevating the importance of K(decadiene/w) as a predictor of molecular bioavailability. On the basis of a 58-point dataset developed by these authors, this research note develops an optimal correlation predicting log(10) K(decadiene/w) in terms of the octanol/water partition coefficient and four of the Abraham solvation parameters, namely A (hydrogen bond acidity), S (polarity/polarizability), E (excess molar refraction), and V (McGowan characteristic volume). The fitted dataset is described to within a root-mean-square error of 0.42, and the probable error in making a prediction for a compound not present therein is 0.49. It is shown that this correlation error for K(decadiene/w) is the dominant source of uncertainty in applying a comprehensive new model of phospholipid bilayer membrane permeability developed in a companion paper (Nitsche and Kasting, submitted for publication), which superposes the effects of molecular size and lipid density upon the decadiene lipophilicity scale. Thus, more experimental studies to augment the limited existing database on K(decadiene/w) are called for.

Thermophysical and excess properties of hydroxamic acids in DMSO

In this work, densities (ρ) and refractive indices (n) of N-o-tolyl-2-nitrobenzo- and N-o-tolyl-4-nitrobenzo-, hydroxamic acids have been determined for dimethyl sulfoxide (DMSO) as a function of their concentrations at T=(298.15, 303.15, 308.15, 313.15, and 318.15)K. These measurements were carried out to evaluate some important parameters, viz, molar volume (V), apparent molar volume (Vϕ), limiting apparent molar volume (Vϕ0), slope (SV∗), molar refraction (RM) and polarizability (α). The related parameters determined are limiting apparent molar expansivity (ϕE0), thermal expansion coefficient (α2) and the Hepler constant (∂2Vϕ0/∂T2). Excess properties such as excess molar volume (VE), deviations from the additivity rule of refractive index (nE), excess molar refraction (RME) have also been evaluated. The excess properties were fitted to the Redlich–Kister equations to estimate their coefficients and standard deviations were determined. The variations of these excess parameters with composition were discussed from the viewpoint of intermolecular interactions in these solutions. The excess properties are found to be either positive or negative depending on the molecular interactions and the nature of solutions. Further, these parameters have been interpreted in terms of solute–solute, solute–solvent interaction and structure making ability of solute in DMSO.

Studies on solution properties of ternary mixture of acetophenone + n-amyl alcohol + dichloromethane and its corresponding binaries at 298.15 K

The excess values of molar volume (V E), viscosity deviation (Δη), deviation in isentropic compressibility (ΔKS ), excess molar refraction (ΔR) and excess Gibbs energy of activation (ΔG*E ) of viscous flow have been investigated from the experimentally measured densities, viscosities, sound speeds and refractive indices for three binary mixtures of acetophenone + n-amyl alcohol, acetophenone + dichloromethane and n-amyl alcohol + dichloromethane and their corresponding ternary mixtures at 298.15 K over the entire composition range. The calculated quantities are further fitted to the Redlich–Kister equation to estimate the binary fitting parameters and standard deviations from the regression lines. The excess or deviation properties were found to be either negative or positive depending on the molecular interactions and the nature of liquid mixtures and have been discussed in terms of molecular interactions and structural changes.

Density, speed of sound, and refractive index measurements for the binary systems (butanoic acid + propanoic acid, or 2-methyl-propanoic acid) at T = (293.15 to 313.15) K

Density, speed of sound, and refractive index for the binary systems (butanoic acid+propanoic acid, or 2-methyl-propanoic acid) were measured over the whole composition range and at T=(293.15, 298.15, 303.15, 308.15, and 313.15)K. The excess molar volumes, isentropic compressibilities, excess isentropic compressibilities, molar refractions, and deviation in refractive indices were also calculated by using the experimental densities, speed of sound, and refractive indices data, respectively. The Redlich–Kister smoothing polynomial equation was used to fit the excess molar volume, excess isentropic compressibility and deviation in refractive index data. The thermodynamic properties have been discussed in terms of intermolecular interactions between the components of the mixtures.

Studies on molecular interaction parameters of hydroxamic acids at different temperatures in DMA

Densities, ρ and refractive indices, n of N-phenylbenzo-, N-o-tolylbenzo- and N-p-tolylbenzo- hydroxamic acids have been determined in N,N′-Dimethylacetamide (DMA) as a function of their concentration at T=(298.15, 303.15, 308.15 and 313.15)K. These measurements were carried out to evaluate some important parameters, viz., apparent molar volume, Vϕ, apparent molar volume at infinite dilution, Vϕ0, molar volume, V, molar refraction, RM, specific refraction, RS and polarizability, α. Partial molar expansibilities, ϕE0, thermal expansion coefficient, α⁎ and Hepler's constant (∂2Vϕ0/∂T2)p have been calculated from the temperature dependence of Vϕ0 values. Excess properties such as excess molar volume, VE, excess refractive index, nE and excess molar refraction, RME have also been evaluated. These parameters have been interpreted in terms of solute–solute, solute–solvent interactions and structure making/breaking ability of solutes in DMA.

Densities, viscosities, refractive indices and excess properties of aniline and o-anisidine with 2-alkoxyethanols at 303.15K

Densities, viscosities and refractive indices have been measured for the binary mixtures of aromatic amines such as aniline and o-anisidine with 2-alkoxyethanols like 2-methoxyethanol, 2-ethoxyethanol and 2-butoxyethanol at 303.15 K. The excess properties are excess molar volume (VE), deviation of viscosity (ηE), deviation of refractive index (ΔnD), excess molar refraction (RmE) and excess Gibbs free energy (ΔG* E) for the six binary mixtures that were calculated and the values are fitted with Redlich–Kister polynomial equation. The measured refractive index values are analyzed by different theoretical mixing rules and the standard deviations are predicted. From the values of excess properties of the binary mixtures and its deviations indicate that a strong specific type of interaction is formed between the amino group (–NH2) of aniline and o-anisidine with hydroxyl group (–OH) of 2-alkoxyethanols. The strength of interaction is in the following order: aniline > o-anisidine in 2-alkoxyethanols (2-BE > 2-EE > 2-ME). Further the hydrogen bonding interaction of anilines with 2-alkoxyethanols is confirmed by FT-IR spectra.

Índices de refracción y densidad de mezclas binarias de heptano con ciclohexano, benceno y tolueno a 293.15, 298.15, 303.15 y 308.15 K

Titulo en ingles: Refraction indexes and density for binary mixtures of heptane with cyclohexane, benzene and toluene at 293.15, 298.15, 303.15KTitulo en portugues: Índices de refração e densidade de misturas binárias de heptano com ciclo-hexano, benzeno e tolueno a 293.15, 298.15, 303.15 e 308.15 KResumen: Se midieron densidades e índices de refracción de mezclas binarias de ciclohexano, benceno y tolueno con heptano a (293.15, 298.15, 303.15 y 308.15) K. El volumen de exceso molar () y el cambio de índice de refracción (dhD) son calculados desde los datos experimentales y ajustados con una ecuación polinomial de Redlich-Kister de orden cuatro.Palabras clave: cambio de índice de refracción, volumen de exceso molar, ecuación de Redlich-Kister, mezclas binarias, hidrocarburos.Abstract: Density and refraction indexes for binary mixtures of cyclohexane, benzene and toluene with heptane (293.15, 298.15, 303.15 and 308.15 K) were measured. Excess molar volume () and refraction index change (dhD)were calculated from experimental data and adjusted with a fourth-order Redlich-Kister polynomial equation.Key words: refraction index change, excess molar volume, Redlich-Kister equation, binary mixture, hydrocarbon.Resumo: Determinam-se densidades e índices de refração de misturas binárias de ciclo-hexano, benzeno e tolueno com heptano a (293.15, 298.15, 303.15 e 308.15) K. Se calcularem os volumes de excesso molar () e o cambio do índice de refração (dhD) a partir dos dados experimentais e ajustados à uma equação polinomial de Redlich-Kister de ordem quatro.Palavras chave: Cambio do índice de refração, volumes de excesso molar, equação de Redlich-Kister, misturas binárias, hidrocarbonetos.

The surface tension, density and refractive index of amino acid ionic liquids: [C3mim][Gly] and [C4mim][Gly

The amino acid ionic liquids (AAILs) [C3mim][Gly] (1-propyl-3-methylimidazolium glycine) and [C4mim][Gly] (1-butyl-3-methylimidazolium glycine) have been prepared by the neutralization method and characterized by 1H NMR spectroscopy and differential scanning calorimetry (DSC). The values of their density, surface tension and refractive index were measured at different temperatures. Since the AAILs can form strong hydrogen bonds with water, small amounts of water are difficult to remove from the AAILs by common methods. In order to eliminate the effect of the impurity as water, the standard addition method (SAM) was applied to these measurements. The values of thermal expansion coefficients, α, surface excess energy, Ea, surface excess entropy, Sa, and molar refraction, Rm, for the AAILs were determined.