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Molecules 2018, 23(1), 163; https://doi.org/10.3390/molecules23010163

Structural Examination of Halogen-Bonded Co-Crystals of Tritopic Acceptors

Department of Chemistry, Kansas State University, Manhattan, KS 66506, USA
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Received: 16 December 2017 / Revised: 9 January 2018 / Accepted: 10 January 2018 / Published: 13 January 2018
(This article belongs to the Special Issue Halogen Bonds and Beyond)
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Abstract

A series of tritopic N-heterocyclic compounds containing electrostatically and geometrically equivalent binding sites were synthesized and subjected to systematic co-crystallizations with selected perfluoroiodoarenes in order to map out their structural landscapes. More than 70% of the attempted reactions produced a co-crystal as indicated by IR spectroscopy. Four new crystal structures are reported and in all of them, at least one potential binding site on the acceptor is left vacant. The absence of halogen bonds to all sites can be ascribed primarily due to deactivation of the σ-hole on the iodo-arene donors and partially due to steric hindrance. The tritopic acceptors containing 5,6-dimethylbenzimidazole derivatives yield discrete tetrameric aggregates in the solid state, whereas the pyrazole and imidazole analogues assemble into halogen-bonded 1-D chains. View Full-Text
Keywords: halogen bond; σ-hole; tritopic acceptor; co-crystals; crystal structures halogen bond; σ-hole; tritopic acceptor; co-crystals; crystal structures
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Andree, S.N.L.; Sinha, A.S.; Aakeröy, C.B. Structural Examination of Halogen-Bonded Co-Crystals of Tritopic Acceptors. Molecules 2018, 23, 163.

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