Affiliation:
1. Institut für Anorganische und Analytische Chemie Goethe-Universität Frankfurt Max-von-Laue-Str. 7 60438 Frankfurt am Main GERMANY
2. Department of Chemistry Clemson University, Advanced Materials Research Laboratory 91 Technology Drive Anderson South Carolina 29625 USA
3. Department of Chemistry Clemson University, Hunter Laboratory 211 S. Palmetto Blvd. Clemson South Carolina 29634 USA
Abstract
AbstractWe recently reported the first examples of S−Cl⋅⋅⋅O halogen bonding complemented by short F⋅⋅⋅F contacts between neighboring chains that resulted in stabilized crystals of ClSO2(CF2)4SO2Cl and ClSO2(CF2)6SO2Cl. More recently, other researchers studied our crystallographic data further using an Independent Gradient Model (IGM), and they suggested if one goes beyond IUPAC's proposed ‘less than the sum of the van der Waals radii’ criterion that even more noncovalent interactions between fluorine atoms on neighboring chains as well as Cl⋅⋅⋅Cl, Cl⋅⋅⋅S, O⋅⋅⋅F, and O⋅⋅⋅S attractive interactions can be found. With that said, we have prepared samples of the related BrSO2(CF2)nSO2Br derivatives (where n=4, 6, 8, and others), which give rise to even stronger S−Br⋅⋅⋅O halogen bonding interactions complemented minimally by O⋅⋅⋅F and F⋅⋅⋅F intermolecular interactions as shown by X‐ray crystallography and computational chemistry using IGM isosurface plots. Additional spectroscopic characterization (multinuclear NMR, FT‐IR, and MS) of the disulfonyl bromide derivatives BrSO2(CF2)4SO2Br, BrSO2(CF2)6SO2Br, and BrSO2(CF2)8SO2Br has also been obtained as well as some preliminary spectroscopic evidence for BrSO2(CF2)2SO2Br and BrSO2CF2O(CF2)2OCF2SO2Br. The implication of these results toward the preparation of the corresponding disulfonyl iodides is discussed.
Funder
National Science Foundation
Subject
General Chemistry,Biochemistry,Organic Chemistry
Cited by
1 articles.
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