3-Methyl-6-nitroindazole in some aqueous co-solvent mixtures: Solubility determination, preferential solvation and solvent effect analysis. (May 2020)

• Record Type: Journal Article
• Authors: Li, Wanxin; Farajtabar, Ali; Xing, Rong; Zhu, Yiting; Zhao, Hongkun; Lv, Rongguan
• Is Part Of: Journal of chemical thermodynamics. Volume 144(2020)
• Publication Date: 2020-05
• Subjects: 3‑Methyl-6-nitroindazole -- Solubility -- Jouyban-Acree -- Preferential solvation -- Solvent effect; Thermodynamics -- Periodicals; Thermochemistry -- Periodicals; Thermodynamique -- Périodiques; Thermochimie -- Périodiques; Thermochemistry; Thermodynamics; Periodicals; 541.369
• DOI: 10.1016/j.jct.2020.106066
• Languages: English
• ISSNs: 0021-9614

Abstract

Graphical abstract: Highlights: 3-Methyl-6-nitroindazole solubility in three aqueous co-solvent mixtures of alcohols was determined and correlated. Preferential solvation of 3-methyl-6-nitroindazole in five mixtures were derived via IKBIs method. Solvent effect was studied in terms of solute-solvent and solvent-solvent interactions. Abstract: The equilibrium solubility of 3-methyl-6-nitroindazole in co-solvent mixtures of acetonitrile (1) + water (2), ethanol (1) + water (2) and n-propanol (1) + water (2) is reported. Experiments were performed by using the saturation shake-flask technique at temperature range from 278.15 to 328.15 K. The maximum solubility value was observed in neat acetonitrile (ethanol or n -propanol) for each co-solvent mixtures. By using the Jouyban-Acree model, the 3-methyl-6-nitroindazole solubility was well correlated obtaining RAD values smaller than 4.50% and RMSD values smaller than 3.36 × 10 −4 . Quantitative values for the local mole fraction of acetonitrile (ethanol, n -propanol, DMF or acetone) and water around the 3-methyl-6-nitroindazole were computed by using the Inverse Kirkwood–Buff integrals method applied to the solubility data. 3-Methyl-6-nitroindazole was preferentially solvated by water in water-rich compositions; while within co-solvent-rich and intermediate compositions, 3-methyl-6-nitroindazole is preferentially solvated by acetonitrile (ethanol, n -propanol, DMF or acetone) in the acetonitrile (ethanol, n -propanol, DMF or acetone) + water mixtures. The experimental solubility data were correlated by Kamlet and Taft linear solvation energy relationships to examine the main factors describing solvent effect. The results showed that the change in cavity formation energy over the composition played the main role on the solubility variation of 3-methyl-6-nitroindazole in all aqueous mixtures.