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Cost is supported by the EU Framework Programme Horizon 2020
 
2/11/2018 (Added to site)
Author(s): Duane Choquesillo-Lazarte, Vinko Nemec and Dominik Cinčić

Halogen bonded cocrystals of active pharmaceutical ingredients: pyrazinamide, lidocaine and pentoxifylline in combination with haloperfluorinated compounds

Journal: CrystEngComm
DOI: 10.1039/c7ce01252g
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In this work, we present the cocrystallization of three model active pharmaceutical ingredients: pyrazinamide, lidocaine and pentoxifylline. As cocrystal coformers, we selected perfluorinated halogen bond donors, 1,4-diiodotetrafluorobenzene (tfib) and 1,4-dibromotetrafluorobenzene (tfbb). From a crystal engineering standpoint, the compounds are interesting due to the presence of various potential donor and acceptor species. The choice of  structurally equivalent, ditopic linear halogen bond donors, although of different donor strength, allowed us to study the competition between hydrogen and halogen bonding in the obtained solids. We have prepared six cocrystals by both mechanochemical synthesis and a conventional solution-based method. The results of our work show that the dominant supramolecular bond in pyrazinamide cocrystals is the X⋯N type halogen bond (where X = Br or I) established with the pyrazinyl nitrogen atom, in lidocaine cocrystals it is the X⋯O type halogen bond, while in pentoxifylline cocrystals it is dependent on the donor strength. In the tfib cocrystals, halogen bonds are established with both the secondary nitrogen atom and the xanthyl oxygen atom, while in the tfbb  cocrystals only Br⋯O halogen bonds are formed.



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