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

Rakesh Puttreddy; Ondřej Jurček; Sandip Bhowmik; Toni Mäkelä; Kari Rissanen

doi:10.1039/c5cc09487a

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

Chem Commun (Camb). 2016 Feb 7;52(11):2338-41. doi: 10.1039/c5cc09487a.

Authors

Rakesh Puttreddy¹, Ondřej Jurček¹, Sandip Bhowmik¹, Toni Mäkelä¹, Kari Rissanen¹

Affiliation

¹ University of Jyvaskyla, Department of Chemistry, Nanoscience Center, P.O. Box. 35, FI-40014 University of Jyvaskyla, Finland. kari.t.rissanen@jyu.fi.

PMID: 26728962
DOI: 10.1039/c5cc09487a

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't