Thermodynamics Research Center / ThermoML | Journal of Chemical Thermodynamics

Thermodynamic modelling of solubility and preferential solvation for ribavirin (II) in co-solvent mixtures of (methanol, n-propanol, acetonitrile or 1,4-dioxane) + water

Li, X.[Xinbao], Cong, Y.[Yang], Li, W.[Wentian], Yan, P.[Pengyao], Zhao, H.[Hongkun]
J. Chem. Thermodyn. 2017, 115, 74-83
ABSTRACT
The equilibrium solubility of ribavirin in solvent mixtures of {methanol (1) + water (2)}, {n-propanol (1) + water (2)}, {acetonitrile (1) + water (2)} and {1,4-dioxane (1) + water (2)} was determined experimentally by using isothermal dissolution equilibrium method within the temperature range from (278.15 to 318.15) K under atmospheric pressure (101.1 kPa). At the same temperature and mass fraction of methanol (n-propanol, acetonitrile or 1,4-dioxane), the mole fraction solubility of ribavirin is greater in (methanol + water) than in the other three solvent mixtures. The preferential solvation parameters were derived from their thermodynamic solution properties by means of the inverse Kirkwood Buff integrals. The preferential solvation parameters for methanol, n-propanol, acetonitrile or 1,4-dioxane (dx1,3) were negative in the four solvent mixtures with a very wide compositions, which indicated that ribavirin was preferentially solvated by water. Temperature had little effect on the preferential solvation magnitudes. The higher solvation by water could be explained in terms of the higher acidic behaviour of water interacting with the Lewis basic groups of the ribavirin. Besides, the solubility of the drugs was mathematically represented by using the Jouyban-Acree model, van t Hoff-Jouyban-Acree model and Apelblat-Jouyban- Acree model obtaining average relative deviations lower than 1.57% for correlative studies. It is noteworthy that the solubility data presented in this work contribute to expansion of the physicochemical information about the solubility of drugs in binary solvent mixtures and also allows the thermodynamic analysis of the respective dissolution and specific solvation process.
Compounds
# Formula Name
1 C8H12N4O5 Ribavirin
2 CH4O methanol
3 C3H8O propan-1-ol
4 C2H3N acetonitrile
5 C4H8O2 1,4-dioxane
6 H2O water
Datasets
The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type Compound-# Property Variable Constraint Phase Method #Points
  • POMD
  • 1
  • 2
  • 6
  • Mole fraction - 1 ; Liquid
  • Solvent: Mass fraction - 2; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 99
  • POMD
  • 1
  • 3
  • 6
  • Mole fraction - 1 ; Liquid
  • Solvent: Mass fraction - 3; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 99
  • POMD
  • 1
  • 4
  • 6
  • Mole fraction - 1 ; Liquid
  • Solvent: Mass fraction - 4; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 99
  • POMD
  • 1
  • 5
  • 6
  • Mole fraction - 1 ; Liquid
  • Solvent: Mass fraction - 5; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 88
  • POMD
  • 1
  • 2
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 6
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 3
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 4
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 9
  • POMD
  • 1
  • 5
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 8