Article pubs.acs.org/jced
Investigation of Volumetric and Acoustic Properties of Procainamide Hydrochloride in Aqueous Binary and (Water + Amino Acid) Ternary Mixtures at Different Temperatures Doyel M. Bhattacharya,† Dinesh V. Kawadkar,† Chandrashekhar P. Pandhurnekar,‡ Atul V. Wankhade,† Umesh R. Pratap,† and Sangesh P. Zodape*,† †
Department of Chemistry, Visvesvaraya National Institute of Technology, Nagpur, Maharashtra 440 010, India Department of Applied Chemistry, Shri Ramdeobaba College of Engineering and Management, Nagpur, Maharashtra 440 033, India
‡
S Supporting Information *
ABSTRACT: For effective drug design and development, an integrated process utilizing all available information from structural, thermodynamic, and biological studies plays a very important role. To understand the energy basis of molecular interactions utilizing various thermodynamic methods, volumetric and acoustic studies are vital early in the development process of any drug toward an optimal energy interaction profile while retaining a good pharmacological assay. In this article, we are reporting the data of densities (ρ) and speeds of sound (u) of an antiarrhythmic agent, namely, procainamide hydrochloride in an aqueous binary and aqueous solution of amino acids, i.e., L-alanine and L-valine at T = (298.15, 308.15 and 318.15) K. Different thermodynamic parameters such as the apparent molar volume (Vϕ) of the solute, the isentropic compressibility (κs) of the solution, and the apparent molar isentropic compressibility (κϕ) of procainamide hydrochloride in water and aqueous solutions of L-alanine and L-valine have been computed using the density and speed of sound data at different temperatures. The limiting apparent molar volume (V0ϕ) of solute and the limiting apparent molar compressibility (κ0ϕ) of solute in binary and ternary aqueous solutions have been obtained by extrapolating the plots. The results have been interpreted in light of the competing solute−solute and solute−solvent interactions.
1. INTRODUCTION The physiochemical interactions between a drug and functionally important molecules in a living organism comprise the ion−dipole interactions or hydrophobic hydration, covalent bonding, ionic bonding, charge transfer, and hydrogen bonding that are central to understanding the pharmacodynamics and pharmacokinetics of drugs.1 The significance of the drug action with the biological membranes in terms of drug affinity can be viewed as the measure of polar and nonpolar interactions of the molecule within the fluid or membrane.2 The ubiquities of water make it marvelous and also play an important role in many chemicobiological processes.3 Thus, a detailed study of different thermodynamic properties of the drug of interest in the aqueous environment and in the presence of important metabolites such as amino acids, carbohydrates, and salts enables us to clarify the picture of the varied molecular interactions of the cosolutes with hydrophilic and hydrophobic moieties of the drug.4 These interactions can also be extended to understand the conformational stability of proteins in the biological system. The influence of salt on the stability, structure, and properties of proteins has been reported in the literature.5 According to Nagy and Jencks et al.,6 electrolytes can induce dissociation into proteins without any conformational change or denaturation. The complexity in the nature of © XXXX American Chemical Society
proteins makes it difficult to study the interactions of electrolytes such as drugs with proteins. Thus, it is essential to study the solvation behavior of the systems containing low-molecularweight model compounds such as amino acids and drugs. Procainamide hydrochloride is a medication in the antiarrhythmic class used for the treatment of cardiac arrhythmias. It is used to convert new-onset atrial fibrillation.7 The frequeny of the dose of antiarrhythmic drug procainamide for the purpose of increasing its efficacy has to be maintained in an adequate serum concentration. Owing to its short half-life, the frequency of the dose needs to be increased within every 3 or 4 h. The formation of the procainamide-induced antinuclear antibodies is found to be formed after 6 months of treatment, but further research showed that even after long-term therapy with procainamide, some subjects failed to produce any antinuclear antibodies. Also, procainamide can be acetylated to acetanilide and to other reactive and toxic metabolites, which would contradict its efficacy.8 Thus, the thermodynamic study of the drug in the aqueous environment of amino acids is crucial. The volumes and compressibilities are two vital Received: May 18, 2017 Accepted: November 6, 2017
A
DOI: 10.1021/acs.jced.7b00452 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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hydrochloride was prepared using water as solvent. For the preparation of a ternary mixture of procainamide hydrochloride, the solvents used were stock solutions of a water + L-alanine mixture of different molalities (0.025 and 0.05 mol·kg−1) and water + L-valine of different molalities (0.025 and 0.05 mol·kg−1). Stock solutions were prepared in an airtight flask, and proper precautions were taken to avoid losses due to the evaporation of solvent during the study. 2.2. Methods. The density and ultrasonic velocity measurements of binary and ternary mixtures of the drug at different temperatures T = (298.15, 308.15, and 318.15) K were made using a digital densitometer and sound velocity meter (Anton Paar model DSA 5000M). The calibration of the instrument and the procedure was realized in the same manner as prescribed in the literature.4 The reference fluids used for the calibration of the densimeter are ultrapure water and aqueous solutions of NaCl and D-glucose. The results well agreed with the literature values at the experimental temperatures.1,4,10,11 The uncertainty in the density was found on the order of ±0.05 kg·m−3, so the combined expanded uncertainty was calculated to be Uρ(ρ) = 0.1 kg·m−3. For the acoustic measurement, the working frequency of the instrument is 3 MHz, and the uncertainty evaluated at different temperatures, i.e., T = (298.15 to 318.15) K, was found to be equal to 0.5 m·s−1. The combined expanded uncertainty for the same was found to be Uu(u) = 1.0 m·s−1. The temperature is controlled by a built-in Peltier thermostat (PT 100) of the Anton Paar DSA 5000 M instrument having a temperature constancy of ±0.001 K.
properties that enable the understanding of interactions within solution among solute and solvent molecules.9 Currently, no thermodynamic, compressibility, or spectroscopic data have been reported on antiarrhythmic drug procainamide hydrochloride. The contributions of structurally similar essential amino acids such as L-alanine and L-valine that influence the interactions of the drug and the medium with respect to temperature are also scarce. Thus, in this article, we are reporting the values of densities (ρ) and speeds of sound (u) of the aqueous solutions of procainamide hydrochloride and in aqueous solutions of 0.025 and 0.05 m amino acid, i.e., L-alanine and L-valine at T = (298.15 to 318.15) K in an interval of 10 K as a function of concentration. The experimental data has been used for the computation of different derived thermodynamic parameters. The computed results have been interpreted in terms of different interactions existing in the solution among solute and solvent molecules such as hydrogen bonding and solute−solute and solute−solvent interactions.
2. EXPERIMENTAL SECTION 2.1. Materials. Analytical-grade reagent procainamide hydrochloride was procured from Sigma-Aldrich, whereas L-alanine, L-valine, and NaCl were procured from Fischer Scientific. All solutes have mass fraction purities ≥0.99. The drug was used without further purification from an unopened bottle, but the other compounds were dried under high vacuum at T = 358.15 K overnight to remove the moisture content. Solutes were carefully placed in vacuum desiccators, maintaining the conditions as reported in our previous paper.4 Specifications of these solutes are given in Table 1. The solutions were prepared using doubly-distilled Millipore water on a molality basis by the electronic balance (Shimadzu model AUW220D) without buoyancy corrections, having an uncertainty in weight up to ±0.1 mg. The binary system of procainamide
3. RESULTS AND DISCUSSION 3.1. Volumetric Properties. 3.1.1. Apparent Molar Volume. The experimental density values of aqueous solutions of procainamide hydrochloride and procainamide hydrochloride in 0.025 and 0.05 mol·kg−1 aqueous solutions of two
Table 1. Provenance and Mass Fraction Purity of the Chemical Samples
a
Purity as provided by suppliers. B
DOI: 10.1021/acs.jced.7b00452 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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Table 2. Molality (m), Density (ρ), Speed of Sound (u), Apparent Molar Volume (Vϕ), and Apparent Molar Isentropic Compressibility (κϕ) of Procainamide Hydrochloride in Water and in 0.025 and 0.05 mol·kg−1 Aqueous Solutions of L-Alanine and L-Valine at Different Temperatures T = (298.15, 308.15 and 318.15) K at 1.013 × 105 N·m−2 10−3ρ
m mol·kg
−1
0.0000 0.0292 0.0328 0.0430 0.0551 0.0689 0.0760 0.1194 0.1402 0.1715 0.0804 0.0938 0.1119 0.1306 0.1601 0.0000 0.0257 0.0278 0.0489 0.0514 0.0685 0.0699 0.0787 0.0923 0.1024 0.0000 0.0376 0.0457 0.0630 0.0651 0.0721 0.0829 0.0845 0.0911 0.0955 0.0000 0.0379 0.0485 0.0599 0.0977 0.1453 0.1953 0.2350 0.0000 0.0270 0.0367 0.0451 0.0467 0.0635
−3
kg·m
m·s
−1
−1
m ·mol 3
10−3ρ
m mol·kg
−1
−3
kg·m
m·s
1015κϕ
106Vϕ
u −1
−1
m ·N−1·mol−1
m ·mol 3
5
−1
0.0806 0.0923 0.1040 0.1140 0.1225 0.1281
1015κϕ
106Vϕ
u
Table 2. continued
m ·N−1·mol−1 5
T = 298.15 K Procainamide Hydrochloride + Water 0.997043 1497.0 226.92 −35.3 0.998359 1501.6 226.94(±1.71) −28.7(±5.9) 0.998521 1502.1 226.97(±1.52) −26.4(±5.5) 0.998975 1503.6 226.99(±1.16) −21.8(±4.8) 0.999510 1505.4 226.96(±0.91) −18.7(±4.2) 1.000136 1507.5 226.74(±0.73) −17.2(±3.8) 1.000448 1508.5 226.76(±0.66) −15.6(±3.6) 1.002375 1514.9 226.48(±0.62) −13.2(±2.8) 1.003299 1517.9 226.29(±0.53) −12.5(±2.6) 1.004662 1522.6 226.17(±0.45) −12.0(±2.3) 1.000656 1509.1 226.56(±0.42) −15.5(±3.5) 1.001267 1511.1 226.33(±0.38) −14.6(±3.2) 1.002054 1513.8 226.40(±0.36) −13.5(±2.9) 1.002870 1516.6 226.38(±0.31) −12.9(±2.7) 1.004183 1520.9 226.10(±0.29) −12.3(±2.4) Procainamide Hydrochloride + 0.025 mol·kg−1 L-Alanine 0.997765 1498.8 227.34 1.4 0.998929 1502.7 226.64(±1.94) −3.4(±6.3) 0.998982 1503.1 228.15(±1.79) −4.6(±6.0) 0.999935 1506.4 227.34(±1.02) −8.8(±4.5) 1.000074 1506.7 226.77(±0.97) −7.8(±4.4) 1.000818 1509.4 226.95(±0.72) −9.2(±3.8) 1.000895 1509.3 226.71(±0.71) −6.6(±3.7) 1.001264 1510.9 226.97(±0.63) −9.5(±3.5) 1.001848 1513.2 227.04(±0.54) −10.5(±3.2) 1.002336 1514.5 226.54(±0.48) −9.5(±3.1) Procainamide Hydrochloride + 0.05 mol·kg−1 L-Alanine 0.998484 1500.0 227.75 −5.5 1.000144 1505.8 227.54(±1.32) −8.4(±5.1) 1.000501 1507.1 227.45(±1.09) −8.9(±4.6) 1.001268 1509.8 227.27(±0.79) −9.6(±3.9) 1.001361 1510.1 227.24(±0.76) −9.6(±3.9) 1.001685 1511.2 226.93(±0.69) −10.0(±3.7) 1.002162 1512.9 226.89(±0.60) −10.0(±3.4) 1.002231 1513.1 226.86(±0.59) −10.2(±3.4) 1.002520 1514.1 226.86(±0.54) −10.1(±3.2) 1.002695 1514.8 227.00(±0.52) −10.1(±3.2) Procainamide Hydrochloride + 0.025 mol·kg−1 L-Valine 0.997706 1498.9 227.12 −17.5 0.999379 1505.2 227.71(±1.32) −13.5(±5.1) 0.999882 1506.8 226.81(±1.03) −13.9(±4.5) 1.000356 1508.5 227.33(±0.84) −12.3(±4.0) 1.002212 1514.2 225.05(±0.51) −12.9(±3.1) 1.004214 1520.9 225.94(±0.34) −9.8(±2.5) 1.006437 1528.2 225.53(±0.26) −9.4(±2.1) 1.008123 1533.7 225.52(±0.21) −8.5(±1.9) Procainamide Hydrochloride + 0.05 mol·kg−1 L-Valine 0.998248 1501.7 227.12 1.5 0.999464 1505.9 226.72(±1.85) −2.6(±6.1) 0.999900 1507.3 226.73(±1.36) −4.8(±5.2) 1.000273 1508.6 226.70(±1.10) −5.9(±4.7) 1.000347 1508.9 226.70(±1.07) −6.1(±4.6) 1.001108 1511.5 226.42(±0.78) −7.6(±3.9)
0.0000 0.0292 0.0328 0.0430 0.0551 0.0689 0.0760 0.1194 0.1402 0.1715 0.0804 0.0938 0.1119 0.1306 0.1601 0.0000 0.0257 0.0278 0.0489 0.0514 0.0685 0.0699 0.0787 0.0923 0.1024 0.0000 0.0376 0.0457 0.0630 0.0651 0.0721 0.0829 0.0845 0.0911 0.0955 0.0000 0.0379 0.0485 0.0599 0.0977 0.1453 0.1953 0.2350 0.0000 0.0270 0.0367 0.0451 0.0467 C
Procainamide Hydrochloride + 0.05 mol·kg L-Valine 1.001886 1514.1 226.15(±0.62) −8.2(±3.4) 1.002397 1515.9 226.22(±0.54) −8.9(±3.2) 1.002861 1517.6 226.72(±0.48) −8.1(±3.0) 1.003397 1519.1 225.78(±0.43) −9.1(±2.9) 1.003687 1520.8 226.48(±0.40) −10.4(±2.8) 1.004003 1521.4 225.87(±0.39) −9.9(±2.7) T = 308.15 K Procainamide Hydrochloride + Water 0.994029 1520.1 228.52 14.9 0.995314 1524.2 228.58(±1.71) 11.7(±5.7) 0.995471 1524.6 228.62(±1.52) 12.6(±5.3) 0.995914 1525.8 228.66(±1.16) 12.5(±4.6) 0.996435 1527.1 228.65(±0.91) 13.9(±4.1) 0.997048 1528.6 228.39(±0.73) 13.7(±3.6) 0.997346 1529.5 228.50(±0.66) 13.4(±2.5) 0.999225 1534.8 228.21(±0.42) 11.6(±2.7) 1.000124 1537.3 228.03(±0.36) 11.1(±2.5) 1.001458 1541.1 227.87(±0.29) 10.4(±2.2) 0.997550 1530.0 228.28(±0.62) 13.0(±3.4) 0.998140 1531.7 228.11(±0.53) 12.3(±3.1) 0.998919 1533.8 228.06(±0.45) 11.7(±2.8) 0.999706 1536.1 228.11(±0.38) 11.3(±2.6) 1.000984 1539.7 227.85(±0.31) 10.6(±2.3) Procainamide Hydrochloride + 0.025 mol·kg−1 L-Alanine 0.994741 1521.6 229.76 9.3 0.995878 1525.2 228.26(±1.94) 6.9(±6.0) 0.995914 1525.6 230.31(±1.79) 6.6(±5.8) 0.996807 1528.1 230.06(±1.02) 8.6(±4.3) 0.996966 1528.4 228.98(±0.97) 7.9(±4.2) 0.997705 1530.7 228.83(±0.72) 6.9(±3.6) 0.997798 1530.9 228.33(±0.71) 6.4(±3.6) 0.998156 1532.0 228.61(±0.63) 6.3(±3.4) 0.998781 1533.8 228.07(±0.54) 5.4(±3.1) 0.999199 1535.1 228.22(±0.48) 5.4(±2.9) Procainamide Hydrochloride + 0.05 mol·kg−1 L-Alanine 0.995466 1522.7 229.77 13.7 0.997074 1527.9 229.50(±1.32) 7.0(±4.9) 0.997422 1528.9 229.36(±1.09) 7.7(±4.5) 0.998171 1531.3 229.11(±079) 5.9(±3.8) 0.998261 1531.6 229.08(±0.76) 5.8(±3.7) 0.998588 1532.6 228.60(±0.69) 4.9(±3.5) 0.999044 1534.00 228.67(±0.60) 4.8(±3.3) 0.999110 1534.3 228.66(±0.59) 4.2(±3.2) 0.999392 1535.2 228.65(±0.54) 4.2(±3.1) 0.999563 1535.8 228.78(±0.52) 4.1(±3.0) Procainamide Hydrochloride + 0.025 mol·kg−1 L-Valine 0.994661 1521.7 230.28 −0.9 0.996261 1527.2 230.23(±1.32) 2.1(±4.9) 0.996706 1528.7 230.12(±1.03) 2.2(±4.3) 0.997220 1530.2 229.44(±0.84) 1.6(±3.9) 0.998875 1535.3 228.67(±0.51) 1.4(±3.0) 1.001025 1541.4 227.52(±0.34) 1.9(±2.4) 1.003198 1547.6 227.11(±0.26) 2.9(±2.1) 1.004839 1552.6 227.14(±0.21) 3.2(±1.9) Procainamide Hydrochloride + 0.05 mol·kg−1 L-Valine 0.995000 1524.2 228.17 6.6 0.996194 1527.1 228.16(±1.85) 3.9(±5.9) 0.996625 1528.4 228.07(±1.36) 3.7(±5.0) 0.996994 1529.5 227.99(±1.10) 3.4(±4.5) 0.997067 1529.7 227.98(±1.07) 3.4(±4.4) DOI: 10.1021/acs.jced.7b00452 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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Table 2. continued 10−3ρ
m mol·kg
−1
−3
kg·m
Table 2. continued m·s
1015κϕ
106Vϕ
u −1
−1
m ·mol 3
−1
10−3ρ
m −1
m ·N ·mol 5
mol·kg
−1
−1
0.0635 0.0806 0.0923 0.1040 0.1140 0.1225 0.1281
0.0000 0.0292 0.0328 0.0430 0.0551 0.0689 0.0760 0.1194 0.1402 0.1715 0.0804 0.0938 0.1119 0.1306 0.1601 0.0000 0.0257 0.0278 0.0489 0.0514 0.0685 0.0699 0.0787 0.0923 0.1024 0.0000 0.0376 0.0457 0.0630 0.0651 0.0721 0.0829 0.0845 0.0911 0.0955 0.0000 0.0379 0.0485 0.0599 0.0977 0.1453 0.1953 0.2350 0.0000 0.0270 0.0367 0.0451
−3
kg·m
m·s
1015κϕ
106Vϕ
u −1
−1
m ·N−1·mol−1
m ·mol 3
5
−1
Procainamide Hydrochloride + 0.05 mol·kg L-Valine 0.997810 1532.1 227.81(±0.78) 1.9(±3.8) 0.998567 1534.6 227.64(±0.62) 0.1(±3.3) 0.999084 1536.1 227.53(±0.54) 0.6(±3.1) 0.999593 1537.6 227.51(±0.48) 1.0(±2.9) 1.000083 1538.9 226.96(±0.43) 0.9(±2.7) 1.000394 1540.0 227.45(±0.40) 1.5(±2.7) 1.000666 1540.7 227.18(±0.39) 1.4(±2.6) T = 318.15K Procainamide Hydrochloride + Water 0.990208 1536.7 230.36 23.6 0.991460 1538.9 230.43(±1.71) 24.4(±5.5) 0.991615 1539.2 230.42(±1.52) 26.9(±5.2) 0.992050 1540.3 230.39(±1.16) 25.1(±4.5) 0.992563 1541.3 230.32(±0.91) 26.2(±4.0) 0.993168 1542.7 229.98(±0.73) 25.1(±3.6) 0.993461 1543.3 230.08(±0.66) 25.7(±3.4) 0.995305 1547.1 229.77(±0.62) 27.0(±2.7) 0.996189 1548.9 229.58(±0.53) 27.2(±2.5) 0.997488 1551.6 229.49(±0.45) 27.4(±2.2) 0.993641 1543.7 230.12(±0.42) 26.0(±3.3) 0.994212 1544.9 230.00(±0.38) 26.4(±3.0) 0.994982 1546.4 229.84(±0.36) 26.9(±2.8) 27.1(±2.6) 0.995779 1548.0 229.67(±0.31) 0.997035 1550.6 229.39(±0.29) 27.3(±2.3) Procainamide Hydrochloride + 0.025 mol·kg−1 L-Alanine 0.990910 1538.0 230.91 20.7 0.992005 1540.0 230.64(±1.94) 21.9(±5.9) 0.992078 1540.2 231.22(±1.79) 22.5(±5.6) 0.992994 1542.3 230.40(±1.02) 22.3(±4.2) 0.993127 1542.5 229.86(±0.97) 22.5(±4.1) 0.993827 1544.3 230.25(±0.72) 22.4(±3.6) 0.993914 1544.4 229.82(±0.71) 22.1(±3.5) 0.994286 1545.2 229.83(±0.63) 22.7(±3.3) 0.994869 1546.5 229.68(±0.54) 23.3(±3.0) 0.995282 1547.4 229.80(±0.48) 23.7(±2.9) Procainamide Hydrochloride + 0.05 mol·kg−1 L-Alanine 0.991637 1539.2 230.77 23.7 0.993225 1542.3 230.78(±1.32) 24.1(±4.8) 0.993564 1543.0 230.72(±1.09) 25.3(±4.4) 0.994296 1544.9 230.57(±0.79) 23.4(±3.7) 0.994384 1545.1 230.55(±0.76) 23.5(±3.6) 0.994685 1545.7 230.37(±0.69) 23.8(±3.5) 0.995139 1546.7 230.33(±0.60) 24.3(±3.2) 0.995203 1546.9 230.32(±0.59) 24.4(±3.2) 0.995477 1547.5 230.33(±0.54) 24.7(±3.1) 0.995646 1547.9 230.45(±0.52) 24.9(±3.0) Procainamide Hydrochloride + 0.025 mol·kg−1 L-Valine 0.990798 1537.7 230.90 18.4 0.992412 1541.6 230.58(±1.32) 17.9(±4.8) 0.992817 1542.7 231.40(±1.03) 19.6(±4.2) 0.993352 1543.8 230.25(±0.84) 19.3(±3.8) 0.994973 1547.7 229.80(±0.51) 19.9(±3.0) 0.997067 1552.5 228.91(±0.34) 19.6(±2.4) 0.999196 1557.6 228.57(±0.26) 19.4(±2.0) 1.000802 1561.6 228.63(±0.21) 19.5(±1.8) Procainamide Hydrochloride + 0.05 mol·kg−1 L-Valine 0.991103 1540.2 229.25 44.3 0.992286 1542.8 229.28(±1.85) 38.0(±5.7) 0.992709 1543.7 229.31(±1.36) 34.5(±4.9) 0.993074 1544.5 229.23(±1.10) 32.7(±4.4)
0.0467 0.0635 0.0806 0.0923 0.1040 0.1140 0.1225 0.1281
Procainamide Hydrochloride + 0.05 mol·kg L-Valine 0.993146 1544.6 229.22(±1.07) 32.3(±4.3) 0.993881 1546.3 229.05(±0.78) 30.1(±3.7) 0.994630 1547.9 228.87(±0.62) 28.8(±3.3) 0.995141 1549.0 228.76(±0.54) 28.1(±3.0) 0.995654 1550.1 228.64(±0.48) 27.5(±2.9) 0.996091 1551.1 228.54(±0.43) 27.1(±2.7) 0.996425 1551.9 228.77(±0.40) 27.1(±2.6) 0.996675 1552.4 228.66(±0.39) 26.8(±2.6)
Standard uncertainties u are u(T) = 0.001 K, u(m) = 0.0001 mol·kg−1, and u(p) = 0.01 p, and the combined expanded uncertainty is Uρ(ρ) = 0.1 kg·m−3 (k = 2) with a 0.95 level of confidence. bStandard uncertainties u are u(T) = 0.001 K and u(m) = 0.0001 mol·kg−1 and the combined expanded uncertainty Uu(u) = 1.0 m·s−1(k = 2) with a 0.95 level of confidence. a
amino acids, i.e., L-alanine and L-valine, respectively, at temperatures of T = (298.15, 308.15, and 318.15) K have been listed in Table 2. Our experimental values of the density of aqueous binary mixtures of both amino acids at temperatures T = (298.15 and 308.15) K are in good agreement with the literature data.12,13 Figure 1 represents a graphical representation of the density (ρ) of solutions against molality (m) for (procainamide hydrochloride + water) at the studied temperatures. From the figure, it is evident that the density increases with increasing concentration of solute in the solution, whereas its value decreases with increasing temperature of the solution. Similar trends were also observed for the ternary systems of the studied drug. The densities of the solution (ρ) and pure solvent (ρ0) for binary mixtures, i.e., water + procainamide hydrochloride, and ternary systems, i.e., water + amino acid + procainamide hydrochloride, at different temperatures T = (298.15 to 318.15) K in an interval of 10 K were used to calculate the apparent molar volumes (Vϕ) of solutes using the following relation:14,15 Vϕ =
⎡ 1000(ρ − ρ) ⎤ M 0 ⎥ +⎢ ⎢⎣ ⎥⎦ ρ mρρ0
(1)
The apparent molar volumes (Vϕ) for the studied systems of procainamide hydrochloride at the experimental temperatures have been listed in Table 2. The uncertainty in Vϕ values taking into consideration the uncertainties in the density measurements as ±0.05 kg·m−3 at a lower concentration of 0.02 mol·kg−1 for procainamide hydrochloride solutions on calculation is found to be ∼1.71 × 10−6 m3·mol−1, and for a higher concentration of 0.1 mol·kg−1, it was found to be ∼4.46 × 10−7 m3·mol−1. The Redlich−Meyer equation was employed to compute the apparent molar volume on infinite dilution of the solute (V0ϕ) as follows,16 Vϕ = V ϕ0 + A v m1/2 + Svm
(2)
where Av is the Debye- Huckel limiting slope dependent upon the valency and temperature. The Debye−Huckel limiting slopes, Av, for 1:1 electrolyte procainamide hydrochloride at the studied temperatures are calculated according to the literature.17,18 SV is the experimental slope of Vϕ − AVm1/2 against m. It is the volumetric virial coefficient, and it characterizes the pairwise interaction of the solvated species in solution.19,20 Figure 2 represents the variation in Vϕ − AV·m1/2 with respect D
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Figure 1. Representative plot of density (ρ) against molality (m) of aqueous solutions of procainamide hydrochloride at T = (298.15, 308.15, and 318.15) K.
magnitude than SV, which manifests the dominant interactions among the solute and solvent molecules as compared to the solute−solute interactions.22,23 The temperature has a positive influence on the magnitude of the solute−solvent interactions, further strengthening them at higher temperature.18 The values of V0ϕ obtained for both studied systems of procainamide hydrochloride as seen from the perusal of Table 3 are positive and increase with the rise in temperature and concentration of the cosolutes, respectively. This reflects the strong drug−solvent interactions between the drug and both of the amino acids in the ternary solutions, respectively.4 The non-negative values of V0ϕ could also be attributed to the reduction in the electrostriction or hydration from the second solvation layer of the ionic group as a result of the increase in temperature. The apparent molar volume at infinite dilution of the drug molecule in the aqueous environment can be thought of as a combination of the four main contributions24,25 V ϕ0 = V (HB) + V (IN) + V (STR) + V (COUL)
Figure 2. Plot of Vϕ − Avm against molality (m) for aqueous solutions of procainamide hydrochloride at T = (■-■, 298.15; ●-●, 308.15; and ▲-▲, 318.15) K. 1/2
(3)
where V(HB) is the contribution due to hydrogen bonding interactions among the solute and solvent, V(IN) is the intrinsic property of the solute before interactions take place, V(STR) is the overall structural contribution to volume that includes any cavity formation (negative effect) and increases the ice likeness of water (positive effect) as a result of changes in the structure of water, and V(COUL) is electrostriction of solvent caused by columbic interactions among solvent and the drug (negative effect). Thus, it may be concluded that positive effects predominate the negative effects in the studied systems at all temperatures. The values of the standard deviation (σ) for the apparent molar volume of the drug26 have been computed by the given equation,
to molality (m) for procainamide hydrochloride + water at different temperatures. The studied ternary systems also produced similar graphs at all of the temperatures studied in the present work. The values of SV and V0ϕ are listed in Table 3. V0ϕ is a measure of solute−solvent interactions because it reflects the true volume of the solute or the volume change arising from the solute−solvent interactions. The experimental slope (SV) provides the quantitative estimation of the solute− solute interactions. The perusal of Table 4 reveals that negative SV values of procainamide hydrochloride are obtained in the binary as well as ternary systems. The negative values of SV are indicative of the presence of the weaker interactions among the solute molecules in the solution.21 V0ϕ is also greater in
1/2 ⎧ (F(x)exp − F(x)calcd )2 ⎫ ⎪ ⎪ ⎬ σ=⎨ ∑ ⎪ ⎪ k−n ⎩ ⎭
E
(4)
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Table 3. Limiting Apparent Molar Properties (V0ϕ) and (κ0ϕ), Experimental Slope (Sv), Standard Deviation (σ) for the Vϕ Values, and Coefficient of Thermal Expansion (α*) of Procainamide Hydrochloride in Water and in 0.025 and 0.05 mol·kg−1 Aqueous Solutions of L-Alanine and L-Valine T
106V0ϕ
K
m ·mol
298.15 303.15 308.15 313.15 318.15 298.15 303.15 308.15 313.15 318.15 298.15 303.15 308.15 313.15 318.15 298.15 303.15 308.15 313.15 318.15 298.15 303.15 308.15 313.15 318.15
3
−1
103α*
1015(K0ϕ) σ
Sv
−1
−1
m ·N ·mol 5
3.1.2. Partial Molar Volume of Transfer. The limiting apparent molar volume data in the experimentally studied binary and the ternary systems have been used to calculate the partial molar volume of transfer (ΔtrV0ϕ) of procainamide hydrochloride from water to 0.025 and 0.05 mol·kg−1aqueous solutions of both the amino acid solutions using the following equation:
K−1
Δtr Vϕ 0 = V ϕ0
Procainamide Hydrochloride + Water 226.92 −9.62 0.0004 −35.31 228.52
−9.36
0.0034
14.89
(aq alanine/valine)
−22.36
0.0238
9.33
0.78
230.91 −20.42 0.0048 20.70 Procainamide Hydrochloride + 0.05 mol·kg−1 L-Alanine 227.75 −15.96 0.0006 −5.507 229.77
−19.41
0.0015
13.74
0.66
230.77 −12.14 0.0003 23.75 Procainamide Hydrochloride + 0.025 mol·kg−1 L-Valine 227.12 −12.44 0.0009 −17.50 230.28
−19.98
0.0130
−0.94
0.82
230.90 −16.11 0.0145 18.43 Procainamide Hydrochloride + 0.05 mol·kg−1 L-Valine 227.12 −10.28 0.0029 1.53 228.17
−13.66
0.0008
6.60
229.25
−11.64
0.0005
44.34
0.56
Table 4. Transfer Partial Molar Properties ΔtrV0ϕ of Procainamide Hydrochloride in Aqueous L-Alanine and L-Valine Solutions at T = (298.15, 308.15, and 313.15) K 106ΔtrV0ϕ
T
m3·mol−1
K −1
Procainamide Hydrochloride + 0.025 mol·kg L-Alanine 298.15 308.15 318.15 Procainamide Hydrochloride + 0.05 mol·kg−1 L-Alanine 298.15 308.15 318.15 Procainamide Hydrochloride + 0.025 mol·kg−1 L-Valine 298.15 308.15 318.15 Procainamide Hydrochloride + 0.05 mol·kg−1 L-Valine 298.15 308.15 318.15
(water)
(5)
From the above equation, it is clear that solute−solute interactions do not influence the ΔtrV0ϕ values and therefore provide the details of interactions concerning the solute and the solvent. The ΔtrV0ϕ values are listed in Table 4 and have been presented in Figure 3 for both ternary systems. The perusal of the above table shows that the ΔtrV0ϕ values are positive for the studied drug in aqueous solutions of L-alanine at all temperatures, whereas for the drug, ΔtrV0ϕ values are positive for 0.025 mol·kg−1 aqueous solutions of L-valine and negative for 0.05 mol·kg−1 aqueous solutions of L-valine at all of the studied temperatures. The observed positive values of ΔtrV0ϕ for procainamide hydrochloride are the outcome of the varied interactions occurring between the drug moiety and the solvent molecules. These positive values have arisen because of the structure promoter nature of the drug. The reason for such behavior is due to the solvophobic solvation as well as the structural promoter interaction for two cospheres according to the cosphere overlap model.27 The chemical behavior and physical behavior of the water molecules are significantly different in the vicinity of the solute particles in the aqueous environment compared to those of bulk molecules. These form-coordinated water molecules, forming charged ionic spheres encircling the solute moiety. These hydration spheres overlap as a result of the closer approach, leading to the exchange of respective chemical species thus altering the thermodynamic properties.16 The negative values in ΔtrV0ϕ result from considerable overlap of hydration cospheres among the hydrophobic groups and the ionic−hydrophilic−hydrophobic groups.4,12 It was observed that the values of ΔtrV0ϕ increase with the concentration of L-alanine, i.e., from 0.025 to 0.05 mol·kg−1 solution, but then decrease from 0.025 to 0.05 mol·kg−1 L-valine solution at all of the studied temperatures. The increase can be thought of in the light of increased hydrogen bonding between the protonated amino group of the drug and the ionized carboxylic group of the amino acid moiety. The decrease in the ΔtrV0ϕ values can be viewed as a result of the dominant intramolecular hydrogen bonding formation in the amide group of the procainamide hydrochloride group over the interaction between the amino group and the carboxyl group of the drug moiety as a result of the stereochemical or planar effects that resulted in lessened interactions. Similar results have been reported by Kumar et al.28 The negative values of ΔtrV0ϕ obtained for the 0.05 mol·kg aqueous solution of L-valine suggest the dominance of the ion-hydrophobic and interhydrophobic interactions favoring the bulk structure of water.29 3.1.3. Thermal Expansion Coefficient. The thermal expansion coefficient (α*) for procainamide hydrochloride has been computed with the help of the following:
0.75
230.36 −11.18 0.0002 23.61 Procainamide Hydrochloride + 0.025 mol·kg−1 L-Alanine 227.34 −12.49 0.0104 1.42 229.76
− V ϕ0
0.42 1.21 0.55 0.83 1.22 0.41 0.20 1.73 0.54 −0.22 −0.38 −1.11
0 1 ⎡⎢ ∂V ϕ ⎤⎥ α∗ = 0 V ϕ ⎢⎣ ∂T ⎥⎦
k and n are the number of experimental points (excluding the end point) and the order of the polynomial equation, respectively. The estimated (σ) values for Vϕ are reported in Table 3. F
P
(6) DOI: 10.1021/acs.jced.7b00452 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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Figure 3. Representative plot of the partial molar volume of transfer (ΔtrV0ϕ) against T for procainamide hydrochloride in aqueous solutions of 0.025 (red bars) and 0.05 mol·kg−1 (blue bars) L-alanine at temperatures of (298.15, 308.15, and 318.15) K.
According to Cabani et al.,30 the quantization of the solute− solvent interactions can be interpreted by the coefficients of thermal expansion (α*). In Table 3, the values of α* are given at T = 308.15 K. Their values in the table suggest the predominance of solute−solvent interactions in the ternary system as compared to in their respective binary systems. 3.2. Acoustic Study. 3.2.1. Speed of Sound. The ultrasonic speed is one of the vital thermodynamic properties because it elaborately provides illustrations of the varied interactions existing among the molecules of the solute and solvent in the system. Table 2 gives the speed of sound (u) values of the drug for the binary and ternary systems of the studied drug at various experimental temperatures. The values of the speed of sound for L-alanine solution at temperatures of T = (298.15 and 308.15) K have been found to agree well with Pal et al.12 and Kumar et al.13 at T = 318.15 K. Figure 4 gives a pictorial presentation of the speed of sound (u) in solution against molality (m) for aqueous binary systems of procainamide hydrochloride at different temperatures. Similar types of graphs have also been obtained for the other experimentally studied solutions. It is seen from Figure 4 that the speed of sound values increases continuously with the increase in the molality of the solute in the solution at a specific temperature. It is also found that the values of the speed of sound at a particular concentration increase with the rise in temperature of the solution. Similar trend were observed for both ternary systems studied in this work. This kind of trend in the ultrasonic velocity values in any solution with the addition of solute is exhibited by the effective solute−solvent interactions as a result of the greater association of molecules.31 3.2.2. Isentropic Compressibility. Density (ρ) and speed of sound (u) data were used to calculate the isentropic compressibility (κs) of the solution for procainamide hydrochloride in water and 0.025 and 0.05 mol·kg−1 aqueous solutions of both L-alanine and L-valine at different temperatures
T = (298.15, 308.15, and 318.15) K using the well-known Newton−Laplace equation:24 κs = −
1 ⎛⎜ ∂V ⎞⎟ 1 = V ⎝ ∂P ⎠S ρu 2
(7)
Figure 5 shows the variation in the isentropic compressibility (κs) of the solution against the concentration of the chosen drug in an aqueous environment at temperatures of T = (298.15 to 318.15) K in an interval of 10 K. It is observed from Figure 5 that κs values are inversely related to the molality of solute in the solution at a certain temperature. Also, it can be seen from the figure that κS values decreases with increases in temperature. The similar nature of the graphs was observed in the case of both ternary systems. This trend is due to the thermal rupture of the water structure with the rise in temperature around the substituted amide group of the drug moiety, which results in the lowering of the κS values. Also, the hydrophilic −OH groups of the amino acids increase the hydrophilic−ionic interactions.32 3.2.3. Apparent Molar Isentropic Compressibility. The apparent molar isentropic compressibility (κϕ) for procainamide hydrochloride in water and aqueous solutions of L-alanine and L-valine was calculated at different temperatures by using the following equation ⎡ 1000(ρ κs − ρκ0) ⎤ ⎡ Mκ ⎤ 0 ⎥ + ⎢ s⎥ κϕ = ⎢ ⎢⎣ ⎥⎦ ⎣ ρ ⎦ mρρ0
(8)
where ρ0 and ρ are the densities of solvent and solution, respectively, m and M are the molality of the solution and the molecular mass of the solute, and κ0 and κs are the isentropic compressibilities of the solvent and solution, respectively. The calculated values of κϕ for procainamide hydrochloride in water and 0.025 and 0.05 mol·kg−1 aqueous solutions of both G
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Figure 4. Three-dimensional plot showing the variation in the speed of sound (u) of solution as a function of molality (m) for aqueous solutions of procainamide hydrochloride at T = (298.15, 308.15, and 318.15) K.
around the drug rather than the water molecules in the bulk. This can be understood via the effect of the strong attractive interaction, whereas the positive values of κϕ imply that the water molecules around the drug molecule lose their rigidity as a consequence of disordered structure at higher temperatures. The smooth extrapolation of the κϕ against (m)1/2 curve to zero concentration yields values of the limiting apparent molar isentropic compressibility of the solute (κ0ϕ) at the concerned temperatures that are calculated using the following relation, and they are shown in Table 3 κϕ = κϕ0 + Sκ(m)1/2
(9)
where Sκ is the experimental slope. Figure 6 shows the nature of the trend in the values of κϕ for the studied drug in aqueous solution against the square root of molality (m)1/2 at the studied temperatures. Similar graphs have been obtained for the ternary systems. The magnitude of the κ0ϕ value is a measure of the interactions of the solute with the solvent molecules in which the existence of the solute−solute interactions is nullified on infinite dilution.33 It is seen that the values of κ0ϕ are negative at 298.15 K for the binary system and the ternary systems, having 0.05 m alanine and 0.025 m valine as solvents. This can be understood as an outcome of the greater resistance to pressure of the ordered form of the solvent.34 On the other hand, the κ0ϕ values become positive at higher temperatures for aqueous binary systems of procainamide hydrochloride and the ternary systems having 0.05 m alanine and 0.025 m valine as solvents. Such trends are due to the melting of the hydration structures around the drug moiety.1 The more negative values of κϕ0 for procainamide hydrochloride at lower studied temperatures for the ternary systems are responsible for the dominance of the attractive interactions within the drug and the medium. With the increase in temperature, the κ0ϕ values become less negative to positive as a result of the reduction in the extent of hydration around the solute molecule causing
Figure 5. Plot of isentropic compressibility (κs) values of procainamide hydrochloride in aqueous solutions as a function of molality (m) at T = (■-■, 298.15; ●-●, 308.15; and ▲-▲, 318.15) K. L-alanine
and L-valine at different temperatures are listed in Table 2. Considering the uncertainty in the speed of sound (u) to be ±0.5 m·s−1 and the isentropic compressibility (κs) to be ±0.02 × 10−11 m2·N1−, the uncertainties in κϕ at 0.05 and 0.1 mol·kg−1 concentrations of the binary solutions were found to be ±4.09 × 10−15 and ±2.74 × 10−15 m5·N−1. It is observed from Table 2 that the negativity of the κϕ values lessens with rising temperature. The κϕ values are strongly negative for ionic compounds in water, positive for hydrophobic solutes, and moderately negative for hydrophilic solutes.24 This can be understood as a result of enhanced solute−solvent interactions. The negative κϕ values in this work are manifest in the low compressibility of the water molecules H
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(SB/EMEQ-287/2013), Government of India, New Delhi, India for financial support.
■
Figure 6. Variation in the values of apparent molar isentropic compressibility (κϕ) of the drug against m1/2 for aqueous solutions of procainamide hydrochloride at T = (■-■, 298.15; ●-●, 308.15; and ▲-▲, 318.15) K.
some of the structured water molecules to be released from the bulk water, rendering increased compressibility to the solutions at the elevated temperatures.35 These results are in agreement with the volumetric study results.
4. CONCLUSIONS The volumetric and acoustic properties of procainamide hydrochloride in water and in aqueous solutions of L-alanine and L-valine have been reported at different temperatures in the present study. The presence of strong interactions of the solute with the solvent molecules in the experimentally studied systems is manifested by the increasing trend in the limiting apparent molar volume. The trend in the values of the limiting apparent compressibility shows the significant solute and solvent interactions. The drug is found to possess structure-making properties in water and acts as a structure breaker in the presence of both amino acids as also correlated by the volumetric and acoustic studies.
■
ASSOCIATED CONTENT
S Supporting Information *
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.7b00452. The standard and combined expanded uncertainties for the data entries of Table 2 measured using the digital densitometer and sound velocity meter (Anton Paar DSA 5000M) (PDF)
■
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AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. ORCID
Sangesh P. Zodape: 0000-0002-7283-902X Notes
The authors declare no competing financial interest. Funding
The authors are thankful to the UGC (47-659/13/2014 WRO) and the Department of Science and Technology (DST)-SERB I
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