Thermodynamic stability analysis of M-NISOLDIPINE (cas 113578-26-0) polymorphs

Add time:08/23/2019    Source:sciencedirect.com

Two polymorphic crystal forms of M-NISOLDIPINE (cas 113578-26-0) (1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-methylpropyl ester) were characterized by X-ray powder diffraction and IR-spectroscopy. The solubility of the two polymorphs in water at 25, 31, 37, 42, and 49 °C was investigated; the values obtained were used to calculate the thermodynamic parameters of the phase transition. The results show that the two forms A and B are enantiotropic. The temperature of polymorphic phase transition was 47 °C, and the values of ΔGA,Bθ, ΔHA,Bθ, and ΔSA,Bθ at 25 °C were 2.47, 36.01, and 112.48 J · mol−1 · K−1, respectively. Form A is thermodynamically stable below the transition temperature; it accorded with interaction energies of the two forms obtained from Density Function Theory (DFT) calculations on the hydrogen-bonding and π-stacking interactions. The character of the solid-state decomposition, studied using DSC analysis, showed that the activation energies of decomposition of the polymorphs A and B after melting at high temperatures were 109.80 and 59.14 kJ · mol−1, respectively. It is conclusion that melted states of polymorphs A and B reserved “the memories” of their respective crystalline state. Furthermore, phase transition of the polymorphs was not found under solid-state grinding conditions. Moisture sorption/desorption experiments showed that the two forms of m-nisoldipine are nonhygroscopic.

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