Measurement, correlation and dissolution thermodynamics of biological active chalcone in organic solvents at different temperatures

https://doi.org/10.1016/j.jct.2014.03.026Get rights and content

Highlights

  • Solubility of chalcone in maximum in non-polar solvent chloroform.

  • Among different alcohols, Solubility is maximum in 1-butanol and minimum in methanol.

  • The positive ΔH and ΔG suggest endothermic and spontaneous dissolution process.

  • The negative entropy in THF and ethyl acetate suggests more ordered structure in these solutions.

  • The positive entropy suggests less ordered structure in solutions.

Abstract

The present study reports the synthesis, characterization and solubility of (E)-2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one. The compound was synthesized by standard process. The purity was monitored by TLC and confirmation of structure was done by using mass, IR and 1H NMR spectral techniques. Further, solubility study of this synthesized compound was conducted in methanol, ethanol, 1-propanol, 1-butanol, tetrahydrofuran (THF), ethyl acetate (EA), acetone (AC) and chloroform (CF) at temperatures ranging from (293.15 to 323.15) K under atmospheric pressure. Further, the solubility data were correlated against temperature and were found to increase with temperature. The modified Apelblat and Buchowski–Ksiazczak λh equations were used to correlate the experimental solubility data. Further, some thermodynamic parameters such as dissolution enthalpy (ΔH), Gibbs free energy (ΔG) and entropy (ΔS) of mixing have also been calculated. The positive enthalpy and Gibbs free energy values suggest the dissolution process to be endothermic and spontaneous.

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 (Cdouble bondO str.), 1597.11(Cdouble bondC str.), 1485.24–1433.66(Cdouble bondC 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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