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Novel halogen-bonded cocrystals of aromatic aldehydes with 1, 4-diiodotetrafluorobenzenene

Over the past decade, studies of halogen bonding have largely focused on cocrystals of perfluorohalocarbons as classic halogen bond donors. Numerous reports have been published dealing in crystal engineering and synthesis of multicomponent materials containing iodo- substituted perfluorinated donors [1]. In this work, we set out to investigate the binding abilities of a classic halogen bond donor, 1, 4- diiodotetrafluorobenzene (tfib), with acceptors containing various functional groups able to take part in halogen bonding. The acceptors we were interested in are aromatic aldehydes: vanillin (van), 4-(dimethylamino)benzaldehyde (dmaba), 2- hydroxynaphthaldehyde (naph) and 4- pyridinecarboxaldehyde (pca). In order to explore the stoichiometric ratio in the cocrystallization of halogen bond donor and aldehyde pairs, we performed mechanochemical syntheses by liquid- assisted grinding solid reactants in 1:1 and 1:2 donor : aldehyde stoichiometric ratios. We have obtained four cocrystals. In van, dmaba and naph cocrystals, the stoichiometry is 1:2, and halogen bonds are formed between the aldehyde oxygen atom and the iodine atom of tfib. The pca cocrystal stoichiometry is 1:1, and the crystal structure is interesting because pca molecules are in a statistical (50:50) disorder, allowing both I···N and I···O halogen bonds to be formed. [1] V. Nemec, D. Cinčić, Cryst. Eng. Comm. 18 (2016) 7425.

1, 4-diiodotetrafluorobenzene, aldehydes, cocrystals, halogen bonding, mechanochemistry

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