Theoretical study of the conformational equilibrium of 1,4-dioxane in gas phase, neat liquid, and dilute aqueous solutions
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- 作者：Rute Barata-Morgado (1)
M. Luz Sánchez (1)
Ignacio Fdez. Galván (1) (2)
José C. Corchado (1)
M. Elena Martín (1)
Aurora Mu?oz-Losa (1)
Manuel A. Aguilar (1) - 关键词：1 ; 4 ; Dioxane ; ASEP/MD ; QM/MM ; Conformational equilibrium ; Solvent effect
- 刊名：Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta)
- 出版年：2013
- 出版时间：October 2013
- 年：2013
- 卷：132
- 期：10
- 全文大小：550 KB
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M. Luz Sánchez (1)
Ignacio Fdez. Galván (1) (2)
José C. Corchado (1)
M. Elena Martín (1)
Aurora Mu?oz-Losa (1)
Manuel A. Aguilar (1)
1. área de Química Física, Edif. José María Viguera Lobo, Universidad de Extremadura, Avda. de Elvas s/n, 06006, Badajoz, Spain
2. Department of Chemistry, ?ngstr?m, The Theoretical Chemistry Programme, Uppsala University, P.O. Box 518, SE-751 20, Uppsala, Sweden - ISSN：1432-2234
文摘
The conformational equilibrium of 1,4-dioxane in the gas phase, in the pure liquid, and in aqueous solution has been studied by means of the Average Solvent Electrostatic Potential from Molecular Dynamics (ASEP/MD) method and the Integral Equation Formalism for the Polarizable Continuum Model (IEF-PCM). The dioxane molecule was described at the DFT(B3LYP)/aug-cc-pVTZ level. In the three phases, the equilibrium is almost completely shifted toward the chair conformer, with populations of the twist-boat conformers lower than 0.01?%. The equilibrium is dominated by the internal energy of the molecule, as the solute–solvent interaction free energies are very similar in the three conformers considered (chair, 1,4 twist-boat, and 2,5 twist-boat). In the pure liquid, where the dioxane–dioxane interaction is dominated by the Lennard-Jones term, the structure is characteristic of a van der Waals liquid. However, the decrease in the C–H distance from gas phase to solution, the increase in the C–H vibrational frequencies, and the presence of a shoulder in the O–Haxial pair radial distribution function point to the presence of a weak C–H–O hydrogen bond. The analysis of the occupancy maps of water oxygen and hydrogen atoms around the 1,4-dioxane molecule confirms this conclusion. Contrary to what is found in small water-dioxane clusters, in the liquid, there is a preference for oxygen atoms to interact with axial hydrogen atoms to form C–H–O hydrogen bonds. Comparison of ASEP/MD and IEF-PCM results indicates that including specific interactions is very important for an adequate description of the solute–solvent interaction; however, the influence of these interactions does not translate in changes in the relative stability of the conformers because it cancels out when energy differences are calculated.