- Acetals and Ethers. 11. Solubility of Alkyl-Substituted 1,3-Dioxolanes and 1,3-Dioxanes in Water
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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, ΔGto, 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 ΔGto, 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.
- Sokolowski, Adam,Burczyk, Bogdan,Oles, Jan
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p. 807 - 809
(2007/10/02)
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