Cox Courtney E, Phifer Jeremy R, Ferreira da Silva Larissa, Gonçalves Nogueira Gabriel, Ley Ryan T, O'Loughlin Elizabeth J, Pereira Barbosa Ana Karolyne, Rygelski Brett T, Paluch Andrew S
Department of Chemical, Paper and Biomedical Engineering, Miami University, Oxford, OH, 45056, USA.
Departamento de Engenharia Química, Universidade Federal de São João del-Rei, CEP: 36420-000, Ouro Branco, MG, Brazil.
J Comput Aided Mol Des. 2017 Feb;31(2):183-199. doi: 10.1007/s10822-016-0001-6. Epub 2017 Jan 28.
Solubility parameter based methods have long been a valuable tool for solvent formulation and selection. Of these methods, the MOdified Separation of Cohesive Energy Density (MOSCED) has recently been shown to correlate well the equilibrium solubility of multifunctional non-electrolyte solids. However, before it can be applied to a novel solute, a limited amount of reference solubility data is required to regress the necessary MOSCED parameters. Here we demonstrate for the solutes methylparaben, ethylparaben, propylparaben, butylparaben, lidocaine and ephedrine how conventional molecular simulation free energy calculations or electronic structure calculations in a continuum solvent, here the SMD or SM8 solvation model, can instead be used to generate the necessary reference data, resulting in a predictive flavor of MOSCED. Adopting the melting point temperature and enthalpy of fusion of these compounds from experiment, we are able to predict equilibrium solubilities. We find the method is able to well correlate the (mole fraction) equilibrium solubility in non-aqueous solvents over four orders of magnitude with good quantitative agreement.
基于溶解度参数的方法长期以来一直是溶剂配方设计和选择的重要工具。在这些方法中,最近研究表明,改进的内聚能密度分离法(MOSCED)能很好地关联多功能非电解质固体的平衡溶解度。然而,在将其应用于新型溶质之前,需要有限数量的参考溶解度数据来回归必要的MOSCED参数。在此,我们展示了对于溶质对羟基苯甲酸甲酯、对羟基苯甲酸乙酯、对羟基苯甲酸丙酯、对羟基苯甲酸丁酯、利多卡因和麻黄碱,如何使用传统的分子模拟自由能计算或连续介质溶剂中的电子结构计算(在此采用SMD或SM8溶剂化模型)来生成必要的参考数据,从而得到具有预测性的MOSCED。采用这些化合物实验测得的熔点温度和熔化焓,我们能够预测平衡溶解度。我们发现该方法能够很好地关联非水溶剂中(摩尔分数)平衡溶解度在四个数量级范围内的情况,且具有良好的定量一致性。