Cocrystals of caffeine with formylphenoxyaliphatic acids: Syntheses, structural characterization, and biological activity

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• 作者：G.S. Suresh Kumar^a ; P.G. Seethalakshmi^b ; N. Bhuvanesh^c ; S. Kumaresan^a ; ^{skumarmsu@yahoo.com}
• 关键词：Caffeine ; Cocrystal ; Formylphenoxyaliphatic acids ; Synthon ; X-ray diffraction ; Hydrogen bonding
• 刊名：Journal of Molecular Structure
• 出版年：2013
• 出版时间：27 February, 2013
• 年：2013
• 卷：1034
• 期：Complete
• 页码：302-309
• 全文大小：1024 K

文摘

Three organic cocrystals namely, caffeine:p-formylphenoxyacetic acid [(caf)(p-fpaa)] (1) caffeine:o-formylphenoxyacetic acid monohydrate [(caf)(o-fpaa)]H₂O (2) and caffeine:p-formylphenoxypropionic acid [(caf)(p-fppa)] (3) were synthesized and studied by FT-IR, NMR, and single crystal XRD studies. The crystal system of cocrystal [(caf)(p-fpaa)] (1) is monoclinic with space group P21/n and Z = 16, that of cocrystal [(caf)(o-fpaa)]H₂O (2) is triclinic with space group P ? 1 and Z = 2, and that of cocrystal [(caf)(p-fppa)] (3) is monoclinic with space group P21/c and Z = 4. The imidazole-carboxylic acid synthon is observed in all the three cocrystals. The intermolecular hydrogen bonds, OH¡¤¡¤¡¤N and ¦Ð-¦Ð interactions together play a major role in stabilizing the crystal structure of all the three cocrystals. The biological activities of crystals 1-3 were studied.