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2001 (1)
1Author    Jörg Dalluhn, Hans-Heinrich Pröhl, Oliver Moers, Armand Blaschette, PeterG. JonesRequires cookie*
 Title    Polysulfonylamine, CXLVII [1]. Die ersten N,N-disulfonylierten Thioharnstoffe: Synthese von (R S02)2N -C(S)-NMe2 (R = Me, 4-M e-C6H4) und Kristallstruktur der Ditosylverbindung Polysulfonylamines, CXLVII [1]. The First N,N-Disulfonylated Thioureas: Synthesis of (R S 0 2 )2 N -C ( S ) -N M e 2 (R = Me, 4 -M e -C 6 H 4) and Crystal Structure of the Ditosyl Compound  
 Abstract    The moisture-sensitive title compounds were obtained in good yields by treating the corre­ sponding silver salts AgN(S0 2 R) 2 with the thiocarbamoyl chloride Me2 NC(S)Cl in aceto-nitrile. In the NMR solution spectra of the novel thioureas, as recorded at room temperature for 13C and up to 120 °C for 'H, the Me2N group invariably gives rise to two distinct resonan­ ces, reflecting unusually high barriers to rotation about the_C(S)-NMe2 bond. The crystal structure of the ditosyl compound (triclinic, space group P I, X-ray diffraction at -130 °C) contains two independent molecules A and B, in which the bond lengths and angles are nearly identical, whereas the conformations exhibit pronounced discrepancies. The amide N and thiocarbonyl C atoms have trigonal-planar environments, but the S -N -S planes are strikingly rotated into approximately perpendicular orientations relative to the planar C2N -C (S)-N moieties. Other remarkable features of the molecular structures are the exceedingly long C(S)-NS2 bonds [mean: 145.4(3) pm] and the concomitantly short C -S and C(S)-NC2 bonds [mean values: 164.8(2), 132.6(3) pm]. The packing is governed by a three-dimensional system of weak hydrogen bonds and may be viewed as a self-clathrate, in which (B) 2 dimers constructed from C -H —S=C interactions are inserted as guest species into parallel tunnels between (A)oo tapes based upon short C -H — 0=S contacts. 
  Reference    Z. Naturforsch. 56b, 1188—1195 (2001); eingegangen am 4. September 2001 
  Published    2001 
  Keywords    Sulfonylthioureas, Thioamide Single Bond, Weak Hydrogen Bonding 
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 TEI-XML for    default:Reihe_B/56/ZNB-2001-56b-1188.pdf 
 Identifier    ZNB-2001-56b-1188 
 Volume    56