Solubility of 5-Fluorocytosine in Different Pure and Binary Mixed Solvents: Measurement, Model Correlation, Solvent Effect, and Preferential Solvation,Journal of Chemical & Engineering Data

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Solubility of 5-Fluorocytosine in Different Pure and Binary Mixed Solvents: Measurement, Model Correlation, Solvent Effect, and Preferential Solvation
Journal of Chemical & Engineering Data ( IF 2.0 ) Pub Date : 2021-07-21 , DOI: 10.1021/acs.jced.1c00206
Yang Cong ₁ , Cunbin Du ₁ , Meng Wang ₁ , Zhouyu Jiang ₁ , Mingliang Wang ₁

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In this work, the phase equilibrium solubility of 5-fluorocytosine (5-FC) in dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), 1-butanol, acetonitrile, 1-propanol, 1,4-dioxane, acetone, ethyl acetate, 2-propanol, 2-butanone, and mixture systems (DMSO + 2-propanol and DMF + 2-propanol) at a series of temperatures (283.15–323.15 K) is determined, and model correlation, solvent effect, and preferential solvation analysis are researched. The solubility of 5-FC is related to temperature, which decreases with decreasing temperature. For monosolvent systems, the mole solubility order is DMSO > DMF > 1-butanol > 1-propanol > 2-propanol > acetone > 2-butanone > 1,4-dioxane > acetonitrile > ethyl acetate. The solvent effect has been studied in monosolvents, hydrogen-bonding acceptor (HBA) interactions and nonspecific dipolarity/polarizability interactions favor dissolution, and solvent self-cohesiveness is not beneficial to dissolution. For two mixture systems, the mole solubility of 5-FC in DMSO + 2-propanol solvent systems is higher than that in DMF + 2-propanol solvent systems. A dimensionless parameter (δ) is defined to observe the deviation from ideality of mixed solvents whose values are all greater than zero. The equilibrium constant of the solvent exchange process (K_ps) can be used to evaluate the preferential solvation of 5-FC. DMSO or DMF dissolves 5-FC in the local region around 5-FC preferentially. The equilibrium solubility data is correlated by four correlation models (modified Apelblat, λh, CNIBS/R-K, and Jouyban–Acree models). The greatest relative average deviation (RAD) and root-mean-square deviation (RMSD) values are 2.01% and 11.87 × 10^–5 in pure solvent systems and 2.20% and 5.99 × 10^–5 in mixture systems, respectively. These four models show excellent correlation with the experimental solubility data.

中文翻译：

5-氟胞嘧啶在不同纯溶剂和二元混合溶剂中的溶解度：测量、模型关联、溶剂效应和优先溶剂化

在这项工作中，5-氟胞嘧啶 (5-FC) 在二甲基亚砜 (DMSO) 中的相平衡溶解度，N，N-二甲基甲酰胺 (DMF)、1-丁醇、乙腈、1-丙醇、1,4-二恶烷、丙酮、乙酸乙酯、2-丙醇、2-丁酮和混合系统（DMSO + 2-丙醇和 DMF + 2-丙醇）确定了一系列温度 (283.15–323.15 K) 下的，并研究了模型相关性、溶剂效应和优先溶剂化分析。5-FC 的溶解度与温度有关，随着温度的降低而降低。对于单溶剂系统，摩尔溶解度顺序为 DMSO > DMF > 1-丁醇 > 1-丙醇 > 2-丙醇 > 丙酮 > 2-丁酮 > 1,4-二恶烷 > 乙腈 > 乙酸乙酯。已经在单溶剂中研究了溶剂效应，氢键受体 (HBA) 相互作用和非特异性偶极/极化相互作用有利于溶解，溶剂自粘性不利于溶解。对于两种混合体系，5-FC在DMSO+2-丙醇溶剂体系中的摩尔溶解度高于在DMF+2-丙醇溶剂体系中的摩尔溶解度。定义无量纲参数 (δ) 以观察其值均大于零的混合溶剂与理想情况的偏差。溶剂交换过程的平衡常数（K _ps ) 可用于评估 5-FC 的优先溶剂化。DMSO 或 DMF 优先溶解 5-FC 周围的局部区域中的 5-FC。平衡溶解度数据通过四个相关模型（修正的 Apelblat、λ h、CNIBS/RK 和 Jouyban-Acree 模型）相关联。最大的相对平均偏差 (RAD) 和均方根偏差 (RMSD) 值在纯溶剂系统中分别为 2.01% 和 11.87 × 10 ^–5，在混合系统中分别为2.20% 和 5.99 × 10 ^–5。这四个模型与实验溶解度数据显示出极好的相关性。

更新日期：2021-08-12

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