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Very strong (-)N-X(+)(-)O-N(+) halogen bonds. 2016

Rakesh Puttreddy, and Ondřej Jurček, and Sandip Bhowmik, and Toni Mäkelä, and Kari Rissanen
University of Jyvaskyla, Department of Chemistry, Nanoscience Center, P.O. Box. 35, FI-40014 University of Jyvaskyla, Finland. kari.t.rissanen@jyu.fi.

A new (-)N-X(+)(-)O-N(+) paradigm for halogen bonding is established by using an oxygen atom as an unusual halogen bond acceptor. The strategy yielded extremely strong halogen bonded complexes with very high association constants characterized in either CDCl3 or acetone-d6 solution by (1)H NMR titrations and in the solid-state by single crystal X-ray analysis. The obtained halogen bond interactions, RXB, in the solid-state are found to be in the order of strong hydrogen bonds, viz. RXB ≈ RHB.

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