The structural landscape of heteroaryl-2-imidazoles: competing halogen- and hydrogen-bond interactions

作者: Christer B. Aakeröy , Tharanga K. Wijethunga , Mohammad Abul Haj , John Desper , Curtis Moore

DOI: 10.1039/C4CE00803K

关键词: Halogen bondHalogenMoleculeHydrogen bondCrystallographyAcceptorStereochemistryChemistryIntermolecular force

摘要: In order to examine the competition between hydrogen bonds and halogen when confronted with a probe molecule containing multiple potential acceptor sites one hydrogen-bond donor, five heteroaryl-2-imidazoles were synthesized subsequently co-crystallized fifteen different halogen-bond donors. 30 of 75 experiments resulted in formation co-crystals, these produced crystals suitable for single-crystal X-ray diffraction analysis. A systematic analysis primary intermolecular interactions structures shows that bond is formed best site (as predicted by DFT molecular electrostatic surface calculations) demonstrating suitably activated iodine-based donor can compete strong directed assembly solid-state architectures.

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