Preferential solvation of acetaminophen in ethanol + water solvent mixtures according to the inverse kirkwood-buff integrals method

The preferential solvation parameters, i.e., the differences between the local mole fraction of solvents around the solute and those for the bulk co-solvent mixtures in solutions of acetaminophen in ethanol + water binary mixtures were derived from their thermodynamic properties by means of the inverse Kirkwood-Buff integrals (IKBI) method. It is found that acetaminophen is sensitive to solvation effects, so the preferential solvation parameter δxE,A, is negative in water-rich and ethanol-rich mixtures but positive in co-solvent compositions from 0.24 to 0.73 in mole fraction of ethanol. It is conjecturable that in water-rich mixtures the hydrophobic hydration around the aromatic ring and methyl group present in the drug plays a relevant role in the solvation. The more solvation by ethanol in mixtures of similar co-solvent compositions could be due mainly to polarity effects. Finally, the preference of this drug for water in ethanol-rich mixtures could be explained in terms of the bigger acidic behavior of water molecules interacting with the hydrogen-acceptor groups present in acetaminophen such as the carbonyl group.

• Autores: Delgado, Daniel Ricardo; Ángeles Peña, María; Martínez, Fleming
• Tipo de recurso: Article of journal
• Fecha de publicación: 2013
• Institución: Universidad Nacional de Colombia
• Repositorio: Universidad Nacional de Colombia
• Idioma: spa
• OAI Identifier: oai:repositorio.unal.edu.co:unal/50897
• Acceso en línea: https://repositorio.unal.edu.co/handle/unal/50897; http://bdigital.unal.edu.co/44938/; http://bdigital.unal.edu.co/44938/2/
• Palabra clave: acetaminofeno; etanol; solubilidad; integrales inversas de Kirkwood-Buff; IKBI; solvatación preferencial; acetaminophen; ethanol; solubility; inverse Kirkwood-Buff integrals; IKBI; preferential solvation
• Rights: openAccess
• License: Atribución-NoComercial 4.0 Internacional