Structural effects of halogen bonding in iodochalcones.

Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials
Victoria HamiltonSimon R Hall

Abstract

The structures of three iodochalcones, functionalized with fluorine or a nitro group, have been investigated to explore the impact of different molecular electrostatic distributions on the halogen bonding within each crystal structure. The strongly withdrawing nitro group presented a switch of the halogen bond from a lateral to a linear motif. Surprisingly, this appears to be influenced by a net positive shift in charge distribution around the lateral edges of the σ-hole, making the lateral I...I bonding motif less preferable. A channel of amphoteric I...I type II halogen bonds is observed for a chalcone molecule, which was not previously reported in chalcones, alongside an example of the common synthon involving extended linear chains of I...O2N donor-acceptor halogen bonds. This work shows that halogenated chalcones may be an interesting target for developing halogen bonding as a significant tool within crystal engineering, a thus far underexplored area for this common structural motif.

References

Apr 11, 2009·Journal of Medicinal Chemistry·Yunxiang LuWeiliang Zhu
Jan 19, 2010·Journal of the American Chemical Society·Mohammed G SarwarMark S Taylor
Nov 14, 2012·Journal of Medicinal Chemistry·Rainer WilckenFrank M Boeckler
Jul 25, 2013·Chemical Communications : Chem Comm·Srinu Tothadi, Gautam R Desiraju
Jul 31, 2014·IUCrJ·Pierangelo Metrangolo, Giuseppe Resnati
Dec 30, 2014·Acta Crystallographica. Section A, Foundations and Advances·George M Sheldrick
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Apr 7, 2016·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Colin R GroomSuzanna C Ward
May 11, 2017·Chemical Reviews·Chunlin ZhuangZhenyuan Miao
Mar 10, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tzenge-Lien ShihChia-Feng Kuo
Jan 11, 2020·Acta Crystallographica. Section E, Crystallographic Communications·Kieran J SpruceSimon R Hall
Feb 13, 2020·Journal of Applied Crystallography·Clare F MacraePeter A Wood
Oct 30, 2020·Acta Crystallographica. Section E, Crystallographic Communications·Charlie L HallSimon R Hall

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