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Eight compounds of the type (RSO 2 ) 2 N-C(O)-NR' 2  , where R = Me or 4-tolyl and R' = Me, Et,  i Pr or Ph, were obtained in good yields by treating the corresponding carbamoyl chlorides R' 2 NC(0)C1 with silver salts AgN (SO 2 R) 2  in acetonitrile solution. The pronounced sensitivity of the compounds towards atmospheric moisture is indicative of a high degree of electrophilic activation at the carbonyl centre; bulk hydrolysis rapidly leads to carbon dioxide and the corresponding ammonium salt R' 2 NH +  2 'N (SO 2 R) 2 . In the  1 H and  13 C NMR solution spectra, the R4N groups of the ureas give rise to distinct R' resonances at room temperature, reflecting unusually high barriers to rotation about the C(O)-NR' 2  bonds. For ( MeSO 2 ) 2 N-C(O)-NMe 2  (1a) and the analogous ditosyl compound, the  1 H NMR signals of the dimethylamino group were found to coalesce at 107 °C and 93 °C, respectively, which corresponds to a rotational barrier of ⊿G #  c  ≈ 80 kJ mol -1 . In the crystal of la (triclinic, space group P1̄, Z = 2; X-ray diffraction at -75 °C), the molecule possesses an essentially planar Me 2 N-C(O)-N moiety (except H atoms), whereas the C-NS 2  grouping is pyramidalized to such an extent that N lies 27.8(2) pm out of the plane defined by the carbonyl C atom and the two sulfonyl S atoms [S-N-S 120.52(11)°, C-N-S 115.73(14) and 115.06(14)°]. The most remarkable features of the molecular structure are the exceedingly long C(O)-NS 2  bond [148.6(3) pm] and the concomitantly short C-O and C(O)-NC 2  bonds [121.4(3) and 132.2(3) pm]. The crystal packing of la is governed by a three-dimensional network of nine intermolecular C-H···O hydrogen bonds originating from the activated M e-S and M e -N donor groups (H···O 230-266 pm, C-H···O 123-173°).

zeitschrift für naturforschung b

Polysulfonylamine Polysulfonylamine, CXXXVIII [1], 1.1-Di(organosu!fonyl)-3,3-diorganylharnstoffe: Synthese von acht Vertretern und Kristallstruktur des Prototyps (MeSO 2 ) 2 N-C(O)-NMe 2  / Polysulfonylamines, CXXXVIII [1]. 1.1-Di(organosulfonyl)-3,3-diorganylureas: Synthesis of Eight Representatives and Crystal Structure of the Prototype (MeSO 2 ) 2 N-C(O)-NMe 2