Polysulfonylamine, CXL [1]. N-Cycloalkyldimesylamine C„H 2n-1 /N(SO 2 CH 3 ) 2 : Synthesen (n = 3 -6 ), Festkörper-Molekülstrukturen (n = 4 -6 ) Und Rolle Schwacher Wasserstoffbrücken C-H···O In Den Kristallstrukturen

• Published in: Zeitschrift für Naturforschung. B, A journal of chemical sciences Vol. 56; no. 8; pp. 765 - 777
• Main Authors: Schaper, Wiebke, Lange, Ilona, Henschel, Dagmar, Moers, Oliver, Blaschette, Armand, Jones, Peter G.
• Format: Journal Article
• Language: English
• Published: 01.08.2001
• ISSN: 0932-0776; 1865-7117
• DOI: 10.1515/znb-2001-0810

The new disulfonylamines R -N (SO 2 Me) 2 , where R = cyclopropyl (1), cyclobutyl (2), cyclopentyl (3) or cyclohexyl (4), were prepared according to an established one-step procedure (condensation of RNH 2 with two equivalents of MeSO 2 Cl, NaH as basic auxiliary). Whereas the structure determination for 1 was marred by severe disorder, compounds 2 -4 have been characterized by low-temperature X-ray diffraction (2: monoclinic, space group P2 1 Z ' = 2, pseudo-P2 1 /c packing; 3: triclinic, P1̄, Z' - 1; 4: orthorhombic, Pbca, Z ' = 1). The four independent molecules display puckered carbocycles, whereby the electronegative (MeSO 2 ) 2 N substituent occupies an equatorial position, leading to short intramolecular C - H···O contacts (2: angles of ring pucker φ ≈ 30-33°; 3: envelope conformation, φ ≈ 40°; 4: chair conformation, φ 1 ≈ φ 2 51°). In accordance with known congener structures, the C(sp 3 )-N (S) 2 moieties feature trigonal-planar N configurations and unusually long C -N bonds (ranges for 2-4: C -N 148.8-150.8 pm, S -N 166.6-168.9 pm, S -N -S 118.3-119.3°). The three crystal packings are governed by a plethora of weak intermolecular hydrogen bonds C(sp 3 )-H···O , and a thorough survey of these interactions reveals that the inductively activated methyl groups are distinctly more efficient hydrogen bond donors than the methine and methylene ring groups. In each structure, the principal hydrogen bonds create layer substructures parallel to a unit cell face, which are cross-linked by the remaining C -H···O contacts to form three-dimensional networks