127535-47-1Relevant articles and documents
The Reaction of 2,2'-Thiodiethanol with Chloramine-T (Sodium N-Chlorotoluene-p-sulphonamide): Crystal and Molecular Structures of 2,2'-(p-Tolylsulphonylimino-λ4-sulphanyl)diethanol Monohydrate and 2,2'-Sulphinyldiethanol
Ferguson, George,Lough, Alan J.,Glidewell, Christopher,Low, John
, p. 1685 - 1690 (2007/10/02)
Chloramine-T, sodium N-chlorotoluene-p-sulphonamide reacts with 2,2'-thiodiethanol in weakly acidic methanol to yield 2,2'(p-tolylsulphonylimino-λ4-sulphanyl)diethanol monohydrate, MeC6H4-SO2NS(CH2CH2OH)2*H2O (1) and 2,2'-sulphinyldiethanol, OS(CH2CH2OH)2 (2), in yields of 23 and 36percent respectively.Crystals of (1) are monoclinic, space group P21/c, with a = 7.497(1), b = 16.291(2), c = 11.843(2) Angstroem, β = 92.52(1) deg, and Z = 4.The structure was refined from diffractometer data to an R value of 0.033.The structure consists of a hydrogen-bonded array of MeC6H4SO2NS(CH2CH2OH)2 molecules and of water molecules, in which each molecule participates in three hydrogen bonds.Within the MeC6H4SO2NS(CH2CH2OH)2 molecules the S(VI)-N and N-S(IV) bond lengths are 1.602(2) and 1.629(2) Angstroem, and there is a short intramolecular O...S contact distance of 2.931 Angstroem.The structural data indicate a highly polarised, ylidic, molecule.Crystals of (2) are monoclinic, space group P21/n with a = 11.057(4), b = 4.837(2), c = 12.332(4) Angstroem, β = 103.61(3) deg, and Z = 4.The crystals are always twinned, but by careful photographic and diffractometer studies a complete structural analysis was possible; R = 0.044 from 1056 diffractometer data.The structure contains OS(CH2CH2OH)2 molecules which are not maximally extended but which are linked by O-H...O hydrogen bonds to form centrosymmetric dimers, further linked into infinite spirals.The sulphur atom in (2) is pyramidal with an S-O distance of 1.514(3) Angstroem and S-C dictances of 1.789(3) and 1.791(3) Angstroem.