Acetals and Ethers. 11. Solubility of Alkyl-Substituted 1,3-Dioxolanes and 1,3-Dioxanes in Water

Article abstract of DOI:10.1021/j150648a038

2-Alkyl-1,3-dioxolanes, 2-alkyl-4-methyl-1,3-dioxolanes, and 2-alkyl-1,3-dioxanes (alkyl: n-C3H7, ...,n-C6H13) were synthesized and their solubilities in E10-4 M aqueous sodium bicarbonate solution at 293.2 K determined.The standard free energies for transfer from aqueous solution to pure liquid phase, ΔG_t^o, were calculated from the solubility data and the contributions of given fragments of molecules to the free energy estimated.The fve-membered 1,3-dioxolane and six-membered 1,3-dioxane rings given fragments of molecules to the free energy contribution ΔG_t^o<-W>, related to the cyclic fragments of the molecules, are +2.84 +/- 0.20 and +2.26 +/- 0.36 kJ mol^-1, respectively.Their hydrophilicity is, however, much weaker than hat of the hydroxy group in normal alcohols.The 1,3-dioxolane ring bearing a methyl group at the C-4 atom has a markedly weaker hydrophilic character.