engleski

Synthesis of a o-hydroxy imine cocrystal with I···O(hydroxy) halogen bond motif

A long interest in o-hydroxy imines can be attributed to their photo- and/or thermochromic properties in the solid state which can be tuned by means of cocrystallization [1, 2]. Herein we report an imine cocrystal with halogen bond donor 1, 3, 5-triiodotrifluorobenzene (135tfib). The imine is derived from o-vanillin (ov) and 2- aminobenzonitrile (2abn). From a crystal engineering standpoint, it has various functional groups that can act as halogen bond acceptor sites (hydroxy, methoxy, imino and nitrile groups). We obtained the cocrystal by one-pot grinding [3] of a mixture of ov, 2abn and 135tfib in 1:1:1 molar ratio as well as by crystallization from the solution. The crystal structure determination by single crystal X-ray diffraction reveals that the dominant supramolecular bond in the cocrystal is the I···Ohydroxy halogen bond between the imine acceptor and the halogen bond donor, even though one would expect that a I···Nnitrile will occur [2]. [1] A. Carletta, X. Buol, T. Leyssens, B. Champagne, J. Wouters, J. Phys. Chem. C 120 (2016) 10001. [2] M. Zbačnik, M. Vitković, V. Vulić, I. Nogalo, D. Cinčić, Cryst. Growth Des. 16 (2016) 6381. [3] D. Cinčić, T. Friščić, CrystEngComm 16 (2014) 10169.

cocrystals, halogen bonding, imines, mechanochemistry

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