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Die Kristallstruktur von N,N'-Ditosyl-/7-phenylendiamin, Dichtefunktionaltheorie-Berechnungen von Konformationen und Wasserstoffbrücken-Motive von Sulfonamiden / Interactions in M olecular Crystals, 146 [1, 2], The Crystal Structure of N,N'-Ditosyl-p-phenylenediam ine, Density Functional Theory Calculations of Conformations and Hydrogen Bond Motifs in Sulfonamides

  • Hans Bock , Norbert Nagel and Christian Näther

In a study preceeding the investigation of a novel class of inclusion compounds, the lowtemperature crystal structure o f the host-m olecule N ,N ’-ditosyl-p-phenylenediamine has been determined. It crystallizes in the monoclinic space group P21/N with two formula units in the unit cell, forming layers of hydrogen-bonded molecules. The essential subunits are rigid phenyl rings and flexible sulfonamide linkages C -N(H)-S(O2)-C, the conformations o f which are discussed by comparison with data from the Cambridge Structural Database and based on density functional theory (DFT) as well as semiempirical PM3 calculations for the selected model compounds, N-methyl-methane-, N-methyl-benzene- and N-phenyl-methane-sulfonamide. The torsion angle dependent energy and enthalpy profiles allow estimates o f the rotational barriers around the C -S-N -C bonds. In addition, potential hydrogen bonding by the host molecule is discussed in comparison to analogous carbonic acid derivatives.

Received: 1998-8-19
Published Online: 2014-6-2
Published in Print: 1998-12-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

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