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New J. Chem., 2009, 33, 2344 - 2349, DOI: 10.1039/b9nj00263d
EDA Complexes of N-halosaccharins with N- and O-donor ligands
Darko Dolenc and Barbara Modec
A series of EDA complexes of N-iodosaccharin (NISac) and N-bromosaccharin (NBSac) with nitrogen and oxygen electron-pair donors, NISac·H2O, NISac·THF, NISac·Py, NISac2·Pyz and NBSac2·Pyz, was prepared and examined by X-ray diffraction and NMR. The complexes are relatively stable, crystalline compounds with the ligand bound to the halogen atom in a nearly linear arrangement N–halogen–ligand. The halogen–ligand distances are inversely proportional to the donor ability of the ligand. The interactions between ligand and halogen are stronger for iodine than bromine. The X-ray structure analysis has shown that for some compounds the N–X bond in the halosaccharin moiety is not coplanar with the isothiazole ring, and the quantum-chemical calculations demonstrate a high flexibility of the corresponding angle. Complexes were modelled also by DFT calculations using B3LYP and MPW1K functionals. A better fit of the computed geometry was obtained by the geometry optimization in a polar solvent continuum than in vacuum.
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