Solubility, dissolution thermodynamics and preferential solvation of 4-nitroaniline in (ethanol + water) mixtures

References

• Wu J, Wang J, Farajtabar A, et al. Solubility and solution thermodynamics of 2,6-dichloro-4-nitroaniline in 12 pure solvents at temperatures from 278.15 to 323.15 K. J Chem Eng Data. 2019;64(12):5869–5877.
   Web of Science ®Google Scholar
• Jin J-S, Ning Y-Y, Hu K, et al. Solubility of p -nitroaniline in supercritical carbon dioxide with and without mixed cosolvents. J Chem Eng Data. 2013;58(6):1464–1469.
   Web of Science ®Google Scholar
• Wang Y-X, Ma S, Huang M-N, et al. Ag NPs coated PVDF@TiO2 nanofiber membrane prepared by epitaxial growth on TiO2 inter-layer for 4-NP reduction application. Sep Purif Technol. 2019;227:115700.
   Web of Science ®Google Scholar
• Li X, Cong Y, Du C, et al. Solubility and solution thermodynamics of 2-methyl-4-nitroaniline in eleven organic solvents at elevated temperatures. J Chem Thermodyn. 2017;105:276–288.
   Web of Science ®Google Scholar
• Xie W, Zhang J, Zeng Y, et al. Highly sensitive and selective detection of 4-nitroaniline in water by a novel fluorescent sensor based on molecularly imprinted poly(ionic liquid). Anal Bioanal Chem. 2020;412(23):5653–5661.
   PubMed Web of Science ®Google Scholar
• Latypova AR, Lebedev MD, Rumyantsev EV, et al. Amino-modified silica as effective support of the palladium catalyst for 4-nitroaniline hydrogenation. Catalysts. 2020;10(4):375.
   Web of Science ®Google Scholar
• Zhu J, Li M, Zhang H, et al. Determination and calculation for solubility of m-nitroaniline and its mixture in supercritical carbon dioxide. Chem Eng Res Des. 2014;92(12):2806–2813.
   Web of Science ®Google Scholar
• Cong Y, Du C, Wang J, et al. Determination and thermodynamic modelling for 2-methyl-6-nitroaniline solubility in binary solvent mixtures of ethyl acetate + (methanol, ethanol, n-propanol and isopropanol). J Chem Thermodyn. 2017;105:404–413.
   Web of Science ®Google Scholar
• Li Y, Cong Y, Li C, et al. Solubility and preferential solvation of 2-methyl-4-nitroaniline in mixed solvents of ethyl acetate + (methanol, ethanol, n-propanol and isopropanol). J Chem Thermodyn. 2017;113:71–80.
   Web of Science ®Google Scholar
• Li H, Xie Y, Li Z, et al. 2‑Methoxy-4-nitroaniline solubility in several aqueous solvent mixtures: determination, modeling, and preferential solvation. J Chem Eng Data. 2020;65:2673–2682.
   Web of Science ®Google Scholar
• Zhou Y, Xu R, Wang J, et al. Equilibrium solubility investigation and preferential solvation of 2,6-dichloro-4-nitroaniline dissolved in four aqueous mixtures of isopropanol, acetonitrile, n -propanol, and N -methyl-2-pyrrolidone. J Chem Eng Data. 2020;65(5):2912–2920.
   Web of Science ®Google Scholar
• Xu R, Wang J. Solubility measurement and thermodynamic model correlation and evaluation of 2‑chloro-5-nitroaniline in 12 pure solvents. J Chem Eng Data. 2019;64(4):1357–1365.
   Web of Science ®Google Scholar
• Wang J, Yuan X, Jaubert J-N. 4‑Chloro-2-nitroaniline solubility in several pure solvents: determination, modeling, and solvent effect analysis. J Chem Eng Data. 2020;65:222–232.
   Web of Science ®Google Scholar
• Bao Y, Wu J, Zhao X, et al. 2‑Methoxy-4-nitroaniline solubility in several monosolvents: measurement, correlation, and solvent effect analysis. J Chem Eng Data. 2020;65(2):757–765.
   Web of Science ®Google Scholar
• Higuchi T, Connors KA. Phase solubility techniques. 1965;4:117–212. Adv Anal Chem Instrum.
   Google Scholar
• Jouyban A. Handbook of solubility data for pharmaceuticals. Boca Raton, FL: CRC Press; 2010.
   Google Scholar
• Jouyban A. Review of the cosolvency models for predicting solubility of drugs in water-cosolvent mixtures. J Pharm Pharm Sci. 2008;11(1):32–58.
   PubMed Web of Science ®Google Scholar
• Jouyban A. Review of the cosolvency models for predicting solubility in solvent mixtures: an update. J Pharm Pharm Sci. 2019;22:466–485.
   PubMed Web of Science ®Google Scholar
• Barton AFM, ed. Handbook of solubility parameters and other cohesion parameters . 2nd Boca Raton, FL: CRC Press; 1991.
   Google Scholar
• Marcus Y. The properties of solvents. Chichester, UK: John Wiley & Sons; 1998.
   Google Scholar
• Martin A, Bustamante P, Chun AHC, ed. Physical chemical principles in the pharmaceutical sciences. 4th Philadelphia, PA: Lea & Febiger; 1993.
   Google Scholar
• Connors KA. Thermodynamics of pharmaceutical systems: an introduction for students of pharmacy. Hoboken, NJ: Wiley–Interscience; 2002.
   Google Scholar
• Rubino JT. Cosolvents and cosolvency. In: Swarbrick J, Boylan JC, editors. Encyclopedia of pharmaceutical technology. Vol. 3. New York: Marcel Dekker, Inc.; 1988. p. 375–398.
   Google Scholar
• Fedors RF. A method for estimating both the solubility parameters and molar volumes of liquids. Polym Eng Sci. 1974;14(2):147–154.
   Web of Science ®Google Scholar
• Krug RR, Hunter WG, Grieger RA. Enthalpy-entropy compensation. 1. Some fundamental statistical problems associated with the analysis of van’t hoff and Arrhenius data. J Phys Chem. 1976;80(21):2335–2341.
   Web of Science ®Google Scholar
• Krug RR, Hunter WG, Grieger RA. Enthalpy-entropy compensation. 2. Separation of the chemical from the statistical effect. J Phys Chem. 1976;80:2335–2341.
   Web of Science ®Google Scholar
• Ruidiaz MA, Delgado DR, Martínez F, et al. Solubility and preferential solvation of indomethacin in 1,4-dioxane + water solvent mixtures. Fluid Phase Equilib. 2010;299(2):259–265.
   Web of Science ®Google Scholar
• Bevington PR. Data reduction and error analysis for the physical sciences. New York: McGraw-Hill Book, Co.; 1969, p. 56–65.
   Google Scholar
• Barrante JR. Applied mathematics for physical chemistry. 2nd. ed. Upper Saddle River, NJ: Prentice Hall, Inc.; 1998. 227.
   Google Scholar
• Romero S, Reillo A, Escalera B, et al. The behavior of paracetamol in mixtures of amphiprotic and amphiprotic-aprotic solvents: relationship of solubility curves to specific and nonspecific interactions. Chem Pharm Bull. 1996;44(5):1061–1064.
   Web of Science ®Google Scholar
• Perlovich GL, Kurkov SV, Kinchin AN, et al. Thermodynamics of solutions III: comparison of the solvation of (+)-naproxen with other NSAIDs. Eur J Pharm Biopharm. 2004;57(2):411–420.
   PubMed Web of Science ®Google Scholar
• Tomlinson E. Enthalpy-entropy compensation analysis of pharmaceutical, biochemical and biological systems. Int J Pharm. 1983;13(2):115–144.
   Web of Science ®Google Scholar
• Leffler JE, Grunwald E. Rates and equilibria of organic reactions: as treated by statistical, thermodynamic and extrathermodynamic methods. New York: Dover Publications Inc.; 1989.
   Google Scholar
• Bustamante P, Romero S, Reillo A. Thermodynamics of paracetamol in amphiprotic and amphiprotic-aprotic solvent mixtures. Pharm Pharmacol Commun. 1995;1:505–507.
   Google Scholar
• Pacheco DP, Martínez F. Thermodynamic analysis of the solubility of naproxen in ethanol + water cosolvent mixtures. Phys Chem Liq. 2007;45(5):581–595.
   Web of Science ®Google Scholar
• Martínez F, Peña MA, Bustamante P. Thermodynamic analysis and enthalpy-entropy compensation for the solubility of indomethacin in aqueous and non-aqueous mixtures. Fluid Phase Equilib. 2011;308(1–2):98–106.
   Web of Science ®Google Scholar
• Bustamante P, Romero S, Peña A, et al. Nonlinear enthalpy-entropy compensation for the solubility of drugs in solvent mixtures: paracetamol, acetanilide and nalidixic acid in dioxane-water. J Pharm Sci. 1998;87(12):1590–1596.
   PubMed Web of Science ®Google Scholar
• Marcus Y. On the preferential solvation of drugs and PAHs in binary solvent mixtures. J Mol Liq. 2008;140:61–67.
   Web of Science ®Google Scholar
• Marcus Y. Preferential solvation of drugs in binary solvent mixtures. Pharm Anal Acta. 2017;8(1):1000537.
   Google Scholar
• Marcus Y. Solvent Mixtures: Properties and Selective Solvation, Marcel Dekker, Inc., New York, NY; 2002.
   Google Scholar
• Delgado DR, Peña MA, Martínez F. Preferential solvation of acetaminophen in ethanol + water solvent mixtures according to the inverse Kirkwood-buff integrals method. Rev Colomb Cienc Quím Farm. 2013;42:298–314.
   Google Scholar
• Jiménez DM, Cárdenas ZJ, Delgado DR, et al. Preferential solvation of methocarbamol in aqueous binary cosolvent mixtures at 298.15 K. Phys Chem Liq. 2014;52(6):726–737.
   Web of Science ®Google Scholar
• Kamlet MJ, Taft RW. The solvatochromic comparison method. I. The beta-scale of solvent hydrogen-bond acceptor (HBA) basicities. J Am Chem Soc. 1976;98(2):377–383.
   Web of Science ®Google Scholar
• Ben–Naim A. Preferential solvation in two- and in three-component systems. Pure Appl Chem. 1990;62(1):25–34.
   Web of Science ®Google Scholar
• Marcus Y. Solubility and solvation in mixed solvent systems. Pure Appl Chem. 1990;62(11):2069–2076.
   Web of Science ®Google Scholar