Publicado

2016-05-01

Solution thermodynamics and preferential solvation of 3-chloro-N-phenyl-phthalimide in acetone + methanol mixtures

Termodinámica de soluciones y solvatación preferencial de 3-cloro-N-fenil-ftalimida en mezclas acetona + metanol

DOI:

https://doi.org/10.15446/rcciquifa.v45n2.59941

Palabras clave:

3-Chloro-N-phenylphthalimide, solubility, solution thermodynamics, activity coefficients, preferential solvation (en)
3-cloro-N-fenil-ftalimida, solubilidad, termodinámica de soluciones, coeficiente de actividad, solvatación preferencial (es)

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Autores/as

  • Grecia Angeline del Mar Areiza Aldana Universidad Cooperativa de Colombia
  • Diego Iván Cavides Rubio Universidad Cooperativa de Colombia
  • Gerson Andrés Rodríguez Rodríguez Universidad Nacional de Colombia
  • Aleida Cuellar Lozano Universidad Cooperativa de Colombia
  • Abbas Mehrdad University of Tabriz
  • Daniel Ricardo Delgado Universidad Cooperativa de Colombia
  • Nasly Alexandra Peña Carmona Universidad Cooperativa de Colombia
The thermodynamic properties of the 3-chloro-N-phenyl-phthalimide in acetone + methanol cosolvent mixtures were obtained from solubility data report in literature. The solubility was higher in near acetone and lower in pure methanol at all temperatures studied. A non-linear plot of ∆solnH° vs. ∆solnG° shows a negative slope from pure acetone up to x1 = 0.691. Beyond this composition, a variable positive slope is obtained with the exception of mixtures with x1 = 0.121, x1 = 0.272 and x1 = 0.356 which is a not common trend in these systems. The preferential solvation of 3-chloro-N-phenyl-phthalimide by the components of the solvents was estimated by means of the inverse Kirkwood–Buff integral method, showing the 3-chloro-Nphenyl-phthalimide is preferential solvated by methanol in more polar mixtures and by acetone in less polar ones.

Las propiedades termodinámicas de 3-cloro-N-fenil-ftalimida en mezclas cosolventes acetona + metanol fueron obtenidas a partir de los datos de solubilidad reportados en la literatura. La mayor solubilidad se presentó en acetona y la menor en metanol puro en todas las temperaturas estudiadas. La grafica ΔsolnH° vs. ΔsolnG° presenta una tendencia no lineal, con una pendiente negativa desde la acetona pura hasta x1 = 0,691 a partir de esta composición hasta el metanol puro se obtiene una pendiente positiva variable con la excepción de las mezclas con x1 = 0,121, x1 = 0,272 y x1 = 0,356, la cual es una tendencia poco común en estos sistemas. La solvatación preferencial de 3-cloro-N-fenil-ftalimida por cada uno de los solventes de la mezcla se estimó por medio del método de las integrales inversas de Kirkwood-Buff mostrando que la 3-cloro-N-fenil-ftalimida se solvata preferencialmente por metanol en las mezclas más polares y por acetona en las menos polares.

Referencias

(1) Y. Xie, H. Shi, C. Du, Y. Cong, J. Wang, H. Zhao, Thermodynamic models for determination of 3-chloro-N-phenylphthalimide solubility in binary solvent mixtures of (acetone, ethyl acetate or 1,4-dioxane + methanol), J. Chem. Thermodyn., 100, 22 (2016).

(2) D.R. Delgado, F. Martínez, M.A.A. Fakhree, A. Jouyban, Volumetric properties of the glycerol formal+ water cosolvent system and correlation with the JouybanAcree model, Phys. Chem. Liq., 50, 284 (2012).

(3) D.R. Delgado, M.A. Peña, F. Martínez, Preferential Solvation of some sulfonamides in propylene glycol+ water solvent mixtures according to the IKBI and QLQC methods, J. Solution Chem., 43, 360 (2014).

(4) D.I. Caviedes Rubio, G.A. Rodríguez-Rodríguez, D.R. Delgado, Thermodynamic Study of the solubility of naproxen in some 2-propanol + Water mixtures, Revista Fac. Ciencias B., 12, 48 (2016).

(5) D.I. Caviedes Rubio, R.G. Sotomayor, D.R. Delgado, Solvatación preferencial de la naringina en mezclas cosolventes etanol + agua mediante el método de las integrales inversas de Kirkwood-Buff, Rev. Colomb. Cienc. Quím. Farm., 44, 220 (2015).

(6) D.R. Delgado, O.A. Almanza, F. Martínez, M.A. Peña, A. Jouyban, W.E. Acree Jr., Solution thermodynamics and preferential solvation of sulfamethazine in (methanol + water) mixtures, J. Chem. Thermodyn., 97, 264 (2016).

(7) D.R. Delgado, G.A. Rodríguez, F. Martínez, Thermodynamic study of the solubility of sulfapyridine in some ethanol + water mixtures, J. Mol. Liq., 177, 156 (2013).

(8) D.R. Delgado, F. Martínez, Solution thermodynamics of sulfadiazine in some ethanol+ water mixtures, J. Mol. Liq., 187, 99 (2013).

(9) D.R. Delgado, F. Martínez, Solubility and preferential solvation of sulfadiazine in methanol+ water mixtures at several temperatures, Fluid Phase Equilib., 379, 128 (2014).

(10) D.R. Delgado, F. Martínez, Solubility and preferential solvation of sulfamerazine in methanol + water mixtures at several temperatures, J. Solution Chem., 44, 360 (2015).

(11) R.R. Krug, W.G. Hunter, R.A. Grieger, Enthalpy-entropy compensation. 2. Separation of

The chemical from the statistical effect, J. Phys. Chem., 80, 2341 (1976).

(12) D.R. Delgado, E.F. Vargas, F. Martínez, Thermodynamic study of the solubility of procaine HCl in some ethanol + water cosolvent mixtures, J. Chem. Eng. Data, 55, 2900 (2010).

(13) D.R. Delgado, A. Romdhani, F. Martínez, Solubility of sulfamethizole in some propylene glycol + water mixtures at several temperatures, Fluid Phase Equilib., 322, 113 (2012).

(14) D.R. Delgado, E.F. Vargas, F. Martínez, Preferential solvation of xylitol in ethanol + water solvent mixtures according to the IKBI And QLQC methods, Rev. Colomb. Quím., 42, 59 (2013).

(15) D.R. Delgado, F. Martínez, Preferential solvation of sulfadiazine, sulfamerazine and sulfamethazine in ethanol + water solvent mixtures according to the IKBI method, J. Mol. Liq., 193, 152 (2014).

(16) K.E. Newman, Kirkwood-Buff solution theory: derivation and applications, Chem. Soc. Rev., 23, 31 (1994).

(17) J.A. Lasso, D.I. Caviedes, D.R. Delgado, Preferential solvation of 4-hydroxy-2,5dimethyl-3(2H)-furanone (DMHF) in ethanol + water mixtures according to IKBI and QLQC methods, Ingeniería y Región, 13, 139 (2015).

(18) Y. Marcus, On the preferential solvation of drugs and PAHs in binary solvent mixtures, J. Mol. Liq., 140, 61 (2008).

(19) M.Á Peña, D.R. Delgado, F. Martínez, Preferential solvation of indomethacin in some aqueous co-solvent mixtures, Chem. Eng. Commun., 203, 619 (2016).

(20) A. Ben-Naim, Preferential solvation in two- and in three-component systems, Cell Biophys., 12, 255 (1988).

(21) Y. Marcus, “Solvent mixtures: properties and selective solvation”, Marcel Dekker, Inc., New York, 2002.

(22) C. Du, R. Xu, S. Han, J. Xu, L. Meng, J. Wang, H. Zhao, Solubility of 3-choroN-phenyl-phthalimide, J. Chem. Thermodyn., 96, 187 (2016).

(23) R.F. Fedors, A method for estimating both the solubility parameters and molar volumes of liquids, Polym. Eng. Sci., 14, 147 (1974).

(24) A.F.M. Barton, “Handbook of solubility parameters and other cohesion parameter”, 2nd edition, CRC Press, Inc., New York, 1991.

(25) D.R. Delgado, F. Martínez, Solubility and solution thermodynamics of sulfamerazine and sulfamethazine in some ethanol + water mixtures, Fluid Phase Equilib., 360, 88 (2013).

(26) G.L. Perlovic, S.V. Kurkov, A.N. Kinchin, A. Bauer-Brandl, Thermodynamics of solutions III: comparison of the solvation of (+)-naproxen with other NSAIDs, Eur. J. Pharm. Biopharm., 57, 411 (2004).

(27) G.L. Perlovic, N.N. Strakhova, V.P. Kazachenko, T.V. Volkova, V.V. Tkachev, K.J. Schaper, O.A. Raevsky, Sulfonamides as a subject to study molecular interactions in crystals and solutions: Sublimation, solubility, solvation, distribution and crystal structure, Int. J. Pharm., 349, 300 (2008).

(28) D.R. Delgado, M.A. Ruidiaz, S.M. Gómez, M. Gantiva, F. Martínez, Thermodynamic study of the solubility of sodium naproxen in some ethanol + water mixtures, Quim. Nova, 33, 1923 (2010).

(29) A.R. Holguín, D.R. Delgado, F. Martínez, Thermodynamic study of the solubility of triclocarban in ethanol + propylene glycol mixtures, Quim. Nova, 35, 280(2012).

(30) P. Bustamante, S. Romero, A. Peña, B. Escalera, A. Reillo, Enthalpy-entropy compensation for

The solubility of drugs in solvent mixtures: paracetamol, acetanilide, and nalidixic acid in dioxane-water, J. Pharm. Sci., 87, 1590 (1998).

(31) M. Meloun, Z. Ferencíková, Enthalpy-entropy compensation for some drugs dissociation

In aqueous solutions, Fluid Phase Equilib., 328,31 (2012).

(32) L.P. Pirila-Honkanen, P.A. Ruostesuo, Thermodynamic and spectroscopic properties of 2-pyrrolidinones.1. Excess molar volumes of 2-pyrrolidinone + dichloromethane, + Dimethyl sulfoxide, + acetone, + 2-propanol, and + water, J. Chem. Eng. Data, 32, 303 (1987).

(33) G. Gonfa, M.A Bustam, N. Muhammad, S. Ullah, Density and excess molar volume of binary mixture of thiocyanate-based ionic liquids and methanol at temperatures 293.15-323.15 K, J. Mol. Liq., 211, 734 (2015).

(34) Y. Marcus, “The properties of solvents”, John Wiley & Sons, Inc., New York, 1998.

(35) M.J. Kamlet, R.W. Taft, The solvatochromic comparison method. I. The betascale of solvent hydrogen-bond acceptor (HBA) basicities, J. Am. Chem. Soc., 98, 377 (1976).

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Cómo citar

Areiza Aldana, G. A. del M., Cavides Rubio, D. I., Rodríguez Rodríguez, G. A., Cuellar Lozano, A., Mehrdad, A., Delgado, D. R., & Peña Carmona, N. A. (2016). Termodinámica de soluciones y solvatación preferencial de 3-cloro-N-fenil-ftalimida en mezclas acetona + metanol. Revista Colombiana De Ciencias Químico-Farmacéuticas, 45(2), 256-274. https://doi.org/10.15446/rcciquifa.v45n2.59941