Solubility Modeling, Solvent Effect, and Preferential Solvation of Thiamphenicol in Cosolvent Mixtures of Methanol, Ethanol, N,N-Dimethylformamide, and 1,4-Dioxane with Water
The thiamphenicol solubility in aqueous cosolvent solutions of ethanol (1), methanol (1), 1,4-dioxane (1) and N,N-dimethylformamide (DMF, 1) was measured via the isothermal dissolution equilibrium method at the temperatures ranging from (278.15 to 318.15 K) under local pressure (101.1 kPa). At fixed composition of ethanol (methanol, 1,4-dioxane or DMF) and temperature, the solubility of thiamphenicol was larger in (DMF + water) mixtures than in the ethanol/methanol/1,4-dioxane mixtures. The local solvent proportions were acquired with the method of inverse Kirkwood-Buff integrals. The absolute value of these preferential solvation parameters were all lower than 1.0x10-2 for ethanol (1) + water (2) and 1,4-dioxane (1) + water (2) solutions in water-rich compositions and for methanol (1) + water (2) solutions in whole compositions. In the former two cosolvent mixtures in intermediate compositions and cosolvent-rich regions, thiamphenicol was preferentially solvated by cosolvent. However for the DMF (1) + water (2) solutions, water solvated preferentially thiamphenicol in water-rich compositions and by DMF in intermediate and DMF-rich compositions. This case by cosolvent might be illustrated based on higher basic behavior of water which interacted with Lewis acidic groups of thiamphenicol. In addition, the solubility of thiamphenicol was described with the van't Hoff-Jouyban-Acree, Jouyban-Acree and Apelblat-Jouyban-Acree models. The obtained average relative deviations were no greater than 1.85 %. Furthermore, the solvent effect treatment through KAT-LSER model indicated that the solubility variation was significantly affected by the cavity term.
Compounds
#
Formula
Name
1
C12H15Cl2NO5S
thiamphenicol
2
C2H6O
ethanol
3
CH4O
methanol
4
C4H8O2
1,4-dioxane
5
C3H7NO
dimethylformamide
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.