Experimental investigation of halogen-bond hard-soft acid-base complementarity

The halogen bond (XB) is a topical noncovalent interaction of rapidly increasing importance. The XB employs a `soft' donor atom in comparison to the `hard' proton of the hydrogen bond (HB). This difference has led to the hypothesis that XBs can form more favorable interactions with `soft&#...

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Published inActa crystallographica Section B, Structural science, crystal engineering and materials Vol. 73; no. Pt 2; p. 203
Main Authors Riel, Asia Marie S, Jessop, Morly J, Decato, Daniel A, Massena, Casey J, Nascimento, Vinicius R, Berryman, Orion B
Format Journal Article
LanguageEnglish
Published England Blackwell Publishing Ltd 01.04.2017
Subjects
Acids
Anions - chemistry
Chemical bonds
Crystal structure
Crystallization
Crystallography
Dimethylformamide - chemistry
Dimethylformamide - metabolism
Experiments
Halogens - chemistry
Hydrogen Bonding
Iodides - chemistry
Magnetic Resonance Spectroscopy
NMR titration
halogen bonding
anion recognition
hard–soft acid–base
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Summary:The halogen bond (XB) is a topical noncovalent interaction of rapidly increasing importance. The XB employs a `soft' donor atom in comparison to the `hard' proton of the hydrogen bond (HB). This difference has led to the hypothesis that XBs can form more favorable interactions with `soft' bases than HBs. While computational studies have supported this suggestion, solution and solid-state data are lacking. Here, XB soft-soft complementarity is investigated with a bidentate receptor that shows similar associations with neutral carbonyls and heavy chalcogen analogs. The solution speciation and XB soft-soft complementarity is supported by four crystal structures containing neutral and anionic soft Lewis bases.
ISSN:2052-5192
2052-5206
DOI:10.1107/S2052520617001809