PROCEEDINGS OF THE SHEVCHENKO SCIENTIFIC SOCIETY

Chemical Sciences

Archive / Том LVI 2019

Olena RIDKA1, Vasyl MATIYCHUK2, Irina SOBECHKO1, Nadiia TYSHCHENKO3, Rostislav KOSTYUK1, Volodymyr DIBRIVNYI1, Valentin SERGEEV1

1Department of physical, analytical and general chemistry, Lviv National Polytechnic University, St. Yura pl., 3/4, 79013 Lviv, Ukraine
2Department of Organic Chemistry Lviv National I.Franko University, Kyryla and Mefodiya Str., 6, 79005 Lviv, Ukraine
3Department of Physical Chemistry and Technology of Nanostructured ceramics and nanocomposites Frantsevich Institute for Problems of Materials Science, Krzhizhanovskogo Str., 3, 03142 Kiev, Ukraine

DOI: https://doi.org/10.37827/ntsh.chem.2019.56.080

THERMODYNAMIC PROPERTIES OF SATURATED SOLUTIONS OF METHYL 6-METHYL-4-(4-METHYLPHENYL)-2-OXO-1,2,3,4-ETHRAIDROPYRYMIDINE-5-CARBOXYLATE IN ORGANIC SOLVENTSA

Methyl 6-methyl-4-(4-methylphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate are the simplest representatives of Bidzhenelli’s dyhidropirymidynes and are characterized by a wide range of biological activity. It is important to use pure substances at each stage of the synthesis in the pharmaceutical industry. The main method of solid substances purifying is recrystallization using the so-called "classic" solvents. Therefore, the study of solubility and thermodynamic parameters that accompany the process of solvent interactions with the dissolved substance is important for optimizing the processes of purification and processing of organic compounds. Enthalpy (ΔsolH) and entropy (ΔsolS) of dissolution were determined from the temperature dependence of the solubility of methyl 6-methyl-4-(4-methylphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate in acetonitrile (ΔsolH) = 30.20±0.52 kJ/mol, (ΔsolS) = 38.7±1.7 J/mol∙K, ethyl acetate (ΔsolH) = 27.6±1.0 kJ/mol, (ΔsolS) = 36.0±3.3 J/mol∙K, 2-propanol (ΔsolH) = 36.33±0.52 kJ/mol, (ΔsolS) = 63.5±1.7J/mol∙K and 2-propanone (ΔsolH) = 22.60±0.45kJ/mol, (ΔsolS) = 23.9±1.2J/mol∙K.
Determined values of enthalpy (ΔsolH) and entropy (ΔsolS) of dissolution include values of enthalpy ΔmixH° and entropy ΔmixS° of mixing and a phase transition of crystalline substances to the liquid phase in solution fusH° and fusS°. Fusion enthalpies of substance in kJ/mol ΔfusH487.7=42.6 ± 1.8 were determined from differential thermal analysis (DTA) data obtained using derivatograph Q-1500 D and calculated to 298К ΔfusH (kJ/mol) та fusS° (J/mol∙K): 30.4 ± 1.9, 55.7 ± 2.2 respectively.
The values of enthalpy (ΔmixH°) and entropy (ΔmixS°) of the test substance in acetonitrile are equal to (ΔmixH°) = -0.2±2.0 kJ/mol, (ΔmixS°) = -17.0±2.8 J/mol∙K, ethyl acetate (ΔmixH°) = -2.8±2.1 kJ/mol, (ΔmixS°) = -19.7±4.0 J/mol∙K, 2-propanol (ΔmixH°) = 5.9±2.0 kJ/mol; (ΔmixS°) = 7.8±2.8 J/mol∙K, 2-propanon (ΔmixH°) = -7.8±1.9 kJ/mol; (ΔmixS°) = -31.8±2.5 J/mol∙K. The experimental and calculated data can be used to predict the reactional behavior of the substance in the solution and to optimize the purification and separation processes.

Keywords: dissolution enthalpy, enthalpy mixing, melting enthalpy, dissolution entropy, methyl 6-methyl-4-(4-methylphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate.

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How to Cite

Ridka O., Matiychuk V., Sobechko I., Tyshchenko N., Kostyuk R., Dibrivnyi V., Sergeev V. THERMODYNAMIC PROPERTIES OF SATURATED SOLUTIONS OF METHYL 6-METHYL-4-(4-METHYLPHENYL)-2-OXO-1,2,3,4-ETHRAIDROPYRYMIDINE-5-CARBOXYLATE IN ORGANIC SOLVENTS Proc. Shevchenko Sci. Soc. Chem. Sci. 2019 Vol. LVI. P. 80-88.

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