Halogen and Hydrogen Bonded Complexes of 5-Iodouracil

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• 作者：Arto Valkonen ; Maryna Chukhlieb ; Jani Moilanen ; Heikki M. Tuononen ; Kari Rissanen
• 刊名：Crystal Growth & Design
• 出版年：2013
• 出版时间：November 6, 2013
• 年：2013
• 卷：13
• 期：11
• 页码：4769-4775
• 全文大小：350K
• 年卷期：v.13,no.11(November 6, 2013)
• ISSN：1528-7505

文摘

Three derivatives of 5-iodouracil were prepared, and their complexation properties, supplemented by 5-iodouracil under the same conditions, were studied with and without halogen bond acceptors in N,N-dimethylformamide, N,N-diethylformamide, N-methylformamide, formamide, dimethylsulfoxide, and water. The intermolecular halogen and hydrogen bonding interactions observed in the solid state were investigated using single crystal X-ray diffraction and quantum chemical calculations, and the acquired data were contrasted with bonding interactions previously reported for 5-iodouracil in the Cambridge Structural Database. It was found that the polarized iodine atom and the amidic NH functionality act simultaneously in 5-iodouracil and its derivatives, for which reason the halogen and hydrogen bonds play an equally important role in controlling the resulting crystal structures.