Solid state study of sulfoxide adducts of (2-amidoethyl-C,O)trihalostannanes: Supramolecular networks constructed from hydrogen-bonds involving the amido units

The complex, (H2NCOCH2CH2-C,O)(L))SnCl3, (L = EtCONH2-O), isolated from a reaction mixture containing hydrochloric acid, tin and acrylamide in Et2O solution, undergoes ligand exchange reactions with sulfoxides (sulfoxide = dimethyl sulfoxide, tetramethylene sulfoxide, 2-phenyl-1,3-dithiane trans-1-oxide and 2-phenyl-1,3-dithiane trans-1-trans-3-dioxide) to give (H2NCOCH2CH2-C,O)(sulfoxide-O)SnCl3. The tin centres in all the complexes are hexa-coordinated with a fac-CCl3O2 donor set, in which the octahedral geometries are somewhat distorted due to variations in the Sn–halide bond lengths, exemplifying the trans effect, and the small bite angles of the chelating (2-amidoethyl-C,O) ligand. The 2-phenyl-1,3-dithiane-1,3-dioxide ligand acts only as a monodentate ligand in its complex. The supramolecular structures are dominated by intermolecular hydrogen bonds with the NH2 groups as the donor species. Halide exchange between (H2NCOCH2CH2-C,O)-(tetramethylene sulfoxide-O)SnCl3 and bromide ion was shown to give the mixed halide complex (H2NCOCH2CH2-C,O)(tetramethylene sulfoxide-O)SnCl1.5Br1.5).

The structures and supramolecular arrangements of (H2NCOCH2CH2-C,O)(L-O)SnCl3, (L = dimethyl sulfoxide, tetramethylene sulfoxide, 2-phenyl-1,3-dithiane trans-1-oxide and 2-phenyl-1,3-dithiane trans-1-trans-3-dioxide) are reported.Figure optionsDownload as PowerPoint slideHighlights
► Synthesis is reported of octahedral (H2NCOCH2CH2-C,O)(sulfoxide-O)SnCl3 complexes.
► Crystal and molecular structures of octahedral (H2NCOCH2CH2-C,O)(sulfoxide-O)SnCl3 have been determined.
► Supramolecular arrangements are dominated by intermolecular hydrogen bonds with the NH2 groups as the donor species.