Preferences help
enabled [disable] Abstract
Number of results
2016 | 44 | 13-34
Article title

Solubility of pyrimidine derivatives in different organic solvents at different temperatures

Title variants
Languages of publication
The objective of this study was to measure and correlate the solubility of pyrimidine derivatives in five different solvents namely chloroform, N,N-dimethylformamide, tetrahydrofuran, 1,4-dioxane and ethyl acetate from 298.15 to 328.15 K under atmospheric pressure of 0.1 MPa using gravimetric method. The characterization of all the synthesized compounds was done by IR, NMR and mass spectra. The modified Apelblat and Buchowski-Ksiazczak λh equations were used to correlate the experimental solubility data. Using Van’t Hoff and Gibb’s equations, some thermodynamic parameters such as Gibb’s free energy, enthalpy and entropy of dissolution were evaluated from solubility data. It is found that solubility increases with temperature.
Physical description
  • Physical Chemistry Laboratory, Department of Chemistry, Saurashtra University, Rajkot - 360005 (Gujarat), India
  • [1] Porter, A. E. A.; “Diazines and Benzodiazines.” Vol. 14, Pregamon Press, Elsevier Science BV, Amsterdam, The Netherlands, (1979).
  • [2] Herdewijn, P.; Balzarini, J.; Baba, M.; Pauwels, R.; Aerschot, A. V.; Janssen, G. and Clercq E. D.; “Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides.” J. Med. Chem. 31 (1988) 2040-2048.
  • [3] Prasad, Y. R. and Rahaman S. A.; “Anti-histamine activity of newly synthesized pyrimidines.” Int. J. Chem. Sci. 6 (2008) 2038-2044.
  • [4] Tarnchompoo, B.; Sirichaiwat, C.; Phupong, W.; Intaraudom, C.; Sirawaraporn, W.; Kamchonwongpaisan, S.; Vanichtanankul, J.; Thebtaranonth, Y. and Yuthavong Y.; “Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N Mutants of dihydrofolate reductase from pyrimethamine-resistant plasmodium falciparum.” J. Med. Chem. 45 (2002) 1244-1252.
  • [5] Shakirov, R. R.; Yarmukhamedov N. N.; Vlasova, L. I.; Baibulatova, N. Z.; Yu, R.; Khisamutdinova; Gabdrakhmanova, S. F.; Karachurina, L. T. and Baschenko N. Z.; “Synthesis and antiarrhythmic activity of (1,3-dimethyl-5-nitro-5-hexahydropyrimidinyl)-propionic acid methyl ester.” Pharma. Chem. J. 40 (2006) 29-30.
  • [6] Danesh, A.; Behravan, J. and Ramezani, M.; “Antiviral activity evaluation of some pyrimidine derivatives using plaque reduction assay.” J. Chem. Pharma. Res. 7 (2015) 289-293.
  • [7] Shao, H.; Shenhua, S.; David, W.; Foley, Frankie, L.; Abdullah, Y.; Abbas, Xiangrui, L.; Shiliang, H.; Xiangrui, J.; Baharin, N.; Fischer, P. M. and Shudong, W.; “Synthesis, structure reactivity relationship and biological evaluation of 2,4,5-trisubstituted pyrimidine CDK inhibitors as potential anti-tumor agents.” Eur. J. Med. Chem. 70 (2013) 447-455.
  • [8] Lee, H. W.; Bok, Y. K. and Joong, B. A.; “Molecular design, synthesis, and hypoglycemic and hypolipidemic activities of novel pyrimidine derivatives having thiazolidinedione.” Eur. J. Med. Chem. 40 (2005) 862-874.
  • [9] Juby, P. F.; Hudyma, T. W.; Brown, M.; Essery, J. M. and Partyka, R. A.; “Antiallergy agents. 1. 1,6-dihydro-6-oxo-2- phenylpyrimidine-5-carboxylic acids and esters.” J. Med. Chem. 22 (1979) 263-269.
  • [10] Ren, Y.; Duan, X. and J. Yang, “Experimental measurement and correlation of the solubility of 2-Cyanoguanidine in different pure solvents.” J. Mol. Liq. 191 (2014) 53-58.
  • [11] Wang, F.; Wang, L.; Song, J.; Wang, L. and Chen, H.; “Solubilities of bis(2,2,6,6-tetramethyl-4-piperidinyl) maleate in hexane, heptane, octane, m-xylene and tetrahydrofuran from (253.15 to 310.15) K.” J. Chem. Eng. Data, 49 (2004) 1539-1541.
  • [12] Kumar, A.; Shukla, J. and Mohandas, V. P.; “Effect of pH on the solubility of CaSO4.2H2O in aquious NaCl solutions and physicochemical solution properties at 35 °C.” J. Chem. Eng. Data, 53 (2008) 2797-2800.
  • [13] Guihua, L.; Deng, D.; Chen, Y.; Shan, H. and Ning, A.; “Solubilities and thermodynamic properties of CO2 in choline-chloride based deep eutectic solvents.” J. Chem. Thermo. 75 (2014) 58-62.
  • [14] Buryukin, F. A.; Tverdokhlebov, V. P.; Fedorov, V. A.; Tetenkova, E. V.; Fedorova, A. V. and Azanova, O. O.; “The solubility of acetylferocene and diacetylferocene in dimethylsul foxide and its mixtures with water.” Russ. J. Phy. Chem. A. 82 (2008) 1545-1548.
  • [15] Yuichi, H. and Violette, D.; “Effect of temperature on the solubility of aroma compounds in polyethylene film.” Poly. Test. 25 (2006) 690-696.
  • [16] Milliman, H. W.; Boris, D. and Schiraldi, D. A.; “Experimental determination of Hansen solubility parameters for select poss and polymer compounds as a guide to poss-polymer interaction potentials.” Macromolecules 45 (2012) 1931-1936.
  • [17] Delgado, D. R. and Martinez, F. R.; “Thermodynamic study of the solubility of sodium sulfadiazine in some ethanol + water cosolvent mixtures.” Vitae 17 (2010) 191-198.
  • [18] Jumenez, J. A. and Martinez, F.; “Thermodynamic study of the solubility of acetaminophen in propylene glycol + water cosolvent mixtures.” J. Braz. Chem. Soc. 17 (2006) 125-134.
  • [19] Triana, M. T.; Reyes, A. C.; Jimenez-Kairuz, A. F.; Manzo, R. H. and Martinez, F.; “Solution and mixing thermodynamics of propranolol and atenolol in aqueous media.” J. Sol. Chem. 38 (2009) 73-81.
  • [20] James, W.; Kristina, L.; Mark, P. and Markus, M.; “Surprisingly high solubility of the ionic liquid trihexyltetradecylphosphonium chloride in dense carbon dioxide.” Green Chem. 7 (2005) 475-478.
  • [21] Takashi, K.; “Mutual solubility of hydrophobic ionic liquids and water in liquid-liquid two-phase systems for analytical chemistry.” Anal. Sci. 24 (2008) 1221-1230.
  • [22] Golovanov, A. P.; Hautbergue, G. M.; Wilson, S. A. and Lian, L.; “A simple method for improving protein solubility and long-term stability.” J. Am. Chem. Soc. 126 (2004) 8933-8939.
  • [23] Korolev, V. P.; Antonova, O. A. and Smirnova, N. L.; “Thermodynamics of aqueous L-Proline solutions at 273-323 K.” Russ. J. Physicalchem. A. 84 (2010) 1827-1831.
  • [24] Jackson, A.; Jumenez, and Martinez F.; “Thermodynamic study of the solubility of acetaminophen in propylene glycol + water cosolvent mixtures.” J. Braz. Chem. Soc. 17 (2006) 125-134.
  • [25] Riddick J. A.; Bunger W. B. and Sakano T. “Organic solvents-physical properties and methods of purification.” Techniques of chemistry, New York, (1986).
  • [26] Zhu, M.; “Solubility and density of the disodium salt hemiheptahydrate of ceftriaxone in water + ethanol mixtures.” J. Chem. Eng. Data, 46 (2001) 175-176.
  • [27] Yu, Q.; Ma, X. and Gao, W.; “Determination of the solubility, dissolution enthalpy and entropy of suberic acid in different solvents.” Fluid Phase Equilib. 330 (2012) 44–47.
  • [28] Joly, J.; Nicolau, I. and Armand, M.; “Solubility of α-mercury (II) iodide in dimethyl sulfoxide-methanol and dimethylsulfoxide-ethyl acetate mixtures.” J. Chem. Eng. Data, 24 (1979) 283-285.
  • [29] Apelblat, A. and Manzurola, E.; “Solubility of oxalic, malonic, succinic, adipic, maleic, malic, citric, and tartaric acids in water from 278.15 to 338.15 K.” J. Chem. Thermodyn. 19 (1987) 317-320.
  • [30] Ksiazczak, A.; Moorthi, K. and Nagata, I.; “Solid-solid transition and solubility of even n-alkanes.” Fluid Phase Equilib. 95 (1994) 15-29.
  • [31] Buchowski, H.; Ksiazczak, A. and Pietrzyk, S.; “Solvent activity along a saturation line and solubility of hydrogen-bonding solids.” J. Phys. Chem. 84 (1980) 975-979.
  • [32] Gantiva, M. and Martinez, F.; “Thermodynamic analysis of the solubility of ketoprofen in some propylene glycol+water cosolvent mixtures.” Fluid Phase Equilib. 293 (2010) 242-250.
  • [33] Krug, R. R.; Hunter, W. G. and Grieger, R. A.; “Enthalpy-entropy compensation. 2. Separation of the chemical from the statistical effects.” J. Phys. Chem. 80 (1976) 2341-2351.
  • [34] Meng, Z.; Hu, Y.; Kai, Y.; Yang, W.; Cao, Z. and Shen, F.; “Thermodynamics of solubility of thiomalic acid in different organic solvents from 278.15 K to 333.15 K.” Fluid Phase Equilib. 352 (2013) 1-6.
  • [35] Martin, A.; Physical Pharmacy, 4th edn., Lippincott Williams & Wilkins, Baltimore, USA, 1993.
  • [36] El-Bindary, A. A.; El-Sonbati, A. Z.; El-Mosalamy, E. H.; Ahmed, R. M.; “Potentiomet ric and thermodynamic studies of azosulfonamide drugs X.” Chem. Pap. 57 (2003) 255-258.
Document Type
Publication order reference
YADDA identifier
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.