Analysis of liquid-liquid distribution constants of nonionizable crown ethers and their derivatives

The linear solvation energy relationships (LSER) analysis of the distribution constants of the nonionizable crown ethers between aqueous phase and organic solvents has been carried out applying the cohesive energy density and dimensionless solvatochromic parameters of dipolarity/polarizability, hydrogen donating and accepting abilities of solvents. The molar intrinsic volume and hydrophile-lipophile balance in McGowan scale have been proposed as a descriptors of different crown ethers. The derived correlations permit to predict and/or estimate: (i) distribution constants of nonionizable crown ethers and their benzo derivatives in organic solvent/water systems; (ii) hydration number of crown ethers in the organic phase; (iii) thermodynamic functions followed the distribution of nonionizable crown ethers and their benzo derivatives in organic solvent/water systems; (iv) effect of ionic strength of the aqueous phase and properties of organic solvents on the distribution constants of dicyclohexano-18-crown-6, its alkyl derivatives and higher analogues in the two phase liquid systems