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The halogen bonding proclivity of the aldehyde group in cocrystals of 2-hydroxy-1-naphthaldehyde and perfluorohalogenobenzenes

Throughout our previous work, we have become increasingly interested in the carbonyl oxygen atom as a halogen bond acceptor. In our present work [1], we have decided to test the halogen bonding proclivity of the aldehyde group oxygen atom in competition with the hydroxyl group oxygen atom, and have selected 2-hydroxy-1-naphthaldehyde as the model compound. For cocrystal coformers we have selected haloperfluorinated benzenes, as they are reliable halogen bond donors [2]. We performed a series of mechanochemical experiments, which yielded co crystals with tetrafluoro-1, 4- diiodobenzene, tetrafluoro-1, 3-diiodobenzene, 1, 4-dibromotetrafluorobenzene and trifluoro-1, 3, 5- triiodobenzene. In order to explore the stoichiometric ratio of the coformers in the cocrystal, powder X-ray diffraction and differential scanning calorimetry experiments were performed. Single crystals were obtained by solution-based methods, and their crystal and molecular structures were determined by single crystal X-ray diffraction. In cocrystals containing linear halogen bond donors, molecules participate in C–I∙∙∙Oaldehyde halogen bonds, while in the cocrystal with tetrafluoro-1, 3- diiodobenzene the molecules participate in C– I∙∙∙Ohydroxyl and C–I∙∙∙I halogen bonds.

halogen bonding, perfluorohalogenobenzenes, aldehyde group, 2-hydroxy-1-naphtaldehyde

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