The effects of interactions of dicarboxylic acids on the stability of the caffeine molecule: A theoretical study

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[1] Azizi, Abolfazl
[2] Ebrahimi, Ali
[3] Habibi-Khorassani, Mostafa
[4] Rezazadeh, Shiva
[5] Behazin, Roya
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Azizi, Abolfazl | 1600年 / Chemical Society of Japan卷 / 87期
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The cocrystal formation leads to the improvement of the physicochemical properties of drug substances. Caffeine; as a pharmaceutical compound; forms cocrystals with dicarboxylic acids through OH(acid)...N(caffeine) and CH(caffeine)... O(acid) hydrogen bonds. In the present work; four 2:1 ternary complexes of the caffeine molecule with oxalic; malonic; maleic; and glutaric acids (as cocrystal units) were studied by computational quantum chemistry methods. Also; all ternary complexes were considered in the presence of water molecules. The energy data indicate that the caffeine-oxalic acid complex is the most stable ternary complex with respect to humidity. The results of population analysis; on the basis of the atoms-in-molecules (AIM) and the natural bond orbital (NBO) methods; are in good agreement with the energy data and experimental observations for the caffeine cocrystals. © 2014 The Chemical Society of Japan;
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