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Preferential Solvation of Some Sulfonamides in Propylene Glycol + Water Solvent Mixtures According to the IKBI and QLQC Methods

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Abstract

The preferential solvation parameters, which represent differences between the local and bulk mole fractions of the solvents near to the solute, in solutions of some sulfonamides in propylene glycol + water binary mixtures are derived from their thermodynamic properties by means of the inverse Kirkwood−Buff integrals (IKBI) and the Quasi-Lattice Quasi-Chemical (QLQC) method. From solvent effect studies, it is found that sulfonamides are sensitive to solvation effects; the preferential solvation parameter, δx PG,S, is negative in water-rich mixtures but positive in compositions from 0.20 to 1.00 in mole fraction of propylene glycol according to IKBI method and positive in all co-solvent compositions if the QLQC method is considered. It is conjecturable that in water-rich mixtures, hydrophobic hydration around the aromatic ring and/or other non-polar groups plays a relevant role in the solvation. The greater solvation by propylene glycol mixtures of similar solvent compositions and in co-solvent-rich mixtures could be due mainly to polarity effects and acidic behavior of the sulfonamides, in contrast to the more basic solvent propylene glycol.

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Abbreviations

E :

Pair-wise interactions energy

G :

Molar Gibbs energy; Kirkwood−Buff integral

IKBI:

Inverse Kirkwood−Buff integral

N :

Number of molecules or of neighboring molecule pairs

N A :

Avogadro’s constant

QLQC:

Quasi-Lattice Quasi-Chemical

R :

Gas constant

S :

Molar entropy

SA:

Sulfanilamide

SP:

Sulfapyridine

SMZ:

Sulfamethizole

T :

Absolute temperature

U :

Internal energy

V :

Molar volume

\( \overline{V} \) :

Partial molar volume

x :

Mole fraction

Z :

Quasi-lattice parameter

β :

Kamlet−Taft hydrogen bond acceptor parameter

∆:

Change on transformation

\( \delta x \) :

Preferential solvation parameter

κ T :

Isothermal compressibility

°:

Standard molar

ex:

Excess thermodynamic function

L:

Local

0.5:

Equimolar composition

→:

Transfer

Cor:

Correlation, where preferential solvation occurs

i :

Solvent i

p :

Constant pressure

PG:

Propylene glycol

S:

Solute

T :

Constant absolute temperature

W:

Water

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Authors and Affiliations

  1. Grupo de Investigaciones Farmacéutico Fisicoquímicas, Departamento de Farmacia, Facultad de Ciencias, Universidad Nacional de Colombia, 14490, Bogotá D.C., Colombia

    Daniel Ricardo Delgado & Fleming Martínez

  2. Departamento de Ciencias Biomédicas, Facultad de Farmacia, Universidad de Alcalá, Alcalá de Henares, Madrid, Spain

    María Ángeles Peña

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  1. Daniel Ricardo Delgado
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  2. María Ángeles Peña
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  3. Fleming Martínez
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Correspondence to Fleming Martínez.

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Delgado, D.R., Peña, M.Á. & Martínez, F. Preferential Solvation of Some Sulfonamides in Propylene Glycol + Water Solvent Mixtures According to the IKBI and QLQC Methods. J Solution Chem 43, 360–374 (2014). https://doi.org/10.1007/s10953-014-0130-2

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