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Abstract
Solvent effects on the solubility of a set of structurally related solid compounds (Ax, Ay, etc.) in ethanol-water (system 1) and ethanol-cyclohexane (system 2) are compared by the equation, log Sy = Py log Sx + C. For a given structural change, Ax→Ay, it yields the respective medium-effects parameters, Py1 and Py2. They are used to compare the sensitivity of both solvent systems with the structural changes in the substrates by the equation, Δ12 = (Py1 - 1) - (1 - Py2). Structural changes involving the full replacement of the hydrogen atoms bonded to either O or N afford Δ12 < 0, while those involving solely an increase in the alkyl chain of the substrates yield Δ12 > 0. A structural change where the donor-acceptor capacity of hydrogen bonding is maintained yields a Δ12 approaching zero.
Published Version
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