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N-bromocamphorimide as a chiral halogen bond donor

N-haloimides have recently been recognized as a new class of strong halogen bond donors [1, 2, 3]. There are currently 68 structures in Cambridge Structural Database containing this type of compounds, only 25 of which are halogen bonded cocrystals. As no structures which contain a chiral halogen bond donor have been reported to date, we have decided to attempt preparation of an N-haloimide derived from a chiral acid. We have opted for the naturally occurring (1R, 3S)- camphoric acid as the staring diacid, having thus obtained (1R, 3S)-N-bromocamphorimide (NBCamph), which was characterized by single crystal XRD. This compound has the potential of enantioselective formation of cocrystals, which could prove to be useful in chiral resolution and could also be used for enantioselective bromination of organic compounds. In order to study its potential in formation of cocrystals featuring halogen bonding, we have cocrystalised it with several halogen bond acceptors: 1, 4- diazabicyclo[2.2.2]octane, 4-cyanopyridine, 2, 4, 6-trimethylpyridine, 3, 5-dimethylpyridine, 2- methylpyridine, and 4, 4’-bipyridine. Obtained cocrystals have been characterized using powder XRD and ATR. [1] V. Stilinović, G. Horvat, T. Hrenar, V. Nemec, D. Cinčić, Chem. Eur. J. 23 (2017) 5244. [2] J. Mavračić, D. Cinčić, B. Kaitner, CrystEngComm 18 (2016) 3343. [3] R. W. Troff, T. Mäkelä, F. Topić, A. Valkonen, K. Raatikainen, K. Rissanen, Eur. J. Org. Chem. 2013 (2013) 1617.

N-bromocamphorimide, cocrystals, crystallization

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