Measurement, correlation and dissolution thermodynamics of biological active chalcone in organic solvents at different temperatures
Graphical abstract
Introduction
Chalcones are α, β-unsaturated carbonyl compounds which are mostly present in flavonoids, isoflavonoids and other natural heterocyclic compounds [1], [2], [3]. Most of the chalcones are known to exhibit a wide spectrum of biological activities [4] such as anti-viral [5], anti-cancer [6], anti-inflammatory [7], anti-bacterial [8] and anti-oxidant activities [9] etc. For these reasons, synthesis of chalcones and their functionalized derivatives is a primary objective of the present work.
Further in the pharmaceutical field, solubility and dissolution rates play a prominent role for the discovery and development of drugs [10]. The crystallisation process is a critical method for the purification in pharmaceutical industries for both drug intermediates and final products. Therefore, solubility data are essential for the selection of proper solvents for the crystallisation process and in pre-formulation studies. Further, knowledge of solubility provides necessary information to select a wide range of solvents for the optimization of crystallisation processes [11], [12], [13], [14].
The literature survey shows that the temperature dependent solubility measurement of various drugs and other compounds have been reported in different pure solvents [15], [16], [17], [18], [19], [20], [21].
In this context, the present paper describes the synthesis, characterization and solubility study of synthesized (E)-2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one. The solubility of synthesized chalcone was studied in methanol, ethanol, 1-propanol, 1-butanol, tetrahydrofuran (THF), ethyl acetate (EA), acetone and chloroform (CF) at temperatures ranging from (293.15 to 323.15) K. Also, the experimental solubility data were correlated with the modified Apelblat and Buchowski–Ksiazczak λh equations. Further, the thermodynamic parameters such as enthalpy, Gibbs free energy and entropy of solutions of chalcone have been evaluated.
Section snippets
Materials
(E)-2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one (CD), used in this study was synthesized in our laboratory. The α-tetralone (CAS NO.: 529-34-0) and p-chloro benzaldehyde (CAS NO.: 104-88-1) used in the synthesis were supplied from Spectrochem Pvt. Ltd. (Mumbai, India) and were used without any further treatment. The solvents used in this studied were of AR grade and provided by the same supplier. All solvents were purified by drying over anhydrous sodium sulphate and fractionally
Spectral data
(E)-2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one (CD: IR(cm−1, KBr): 3070.78 (Ar–H asym. str.), 2945.40–2843.17 (CH2 str. of cyclohexanone ring), 1666.55 (CO str.), 1597.11(CC str.), 1485.24–1433.66(CC str. physical nucleus), 1298.14–1089.82(–CH2 bending), 954.80 (ring str. in cyclohexanone), 837 (C–H out of plane bending), 742.62 (C–Cl str.); 1H NMR(DMSO-d6) δ(ppm): 2.938–2.969 (t, 2H, J = 6.4), 3.061–3.090 (t, 2H, J = 6.4), 7.384–7.441 (qt, 2H), 7.524–7.615 (m, 5H), 7.692 (s, 1H),
Conclusions
The solubility of synthesized chalcone in selected solvents is a function of temperature and increases with the rise of temperature. Solubility is maximum in non-polar solvent chloroform and minimum in the polar protic solvent methanol. The modified Apelblat and Buchowski–Ksiazczak λh equations are used to correlate the solubility data and the solubility calculated by these equations shows good agreement with experimental solubility. The calculated solubility of chalcone shows good agreement
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