Halogen and Hydrogen Bonded Complexes of 5-Iodouracil
Valkonen, A., Chukhlieb, M., Moilanen, J., Tuononen, H., & Rissanen, K. (2013). Halogen and Hydrogen Bonded Complexes of 5-Iodouracil. Crystal Growth and Design, 13 (11), 4769-4775. doi:10.1021/cg400924n
Published inCrystal Growth and Design
© 2013 American Chemical Society. This is a final draft version of an article whose final and definitive form has been published by ACS. Published in this repository with the kind permission of the publisher.
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.