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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

12 Issues per year


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1865-7117
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Volume 53, Issue 12 (Dec 1998)

Issues

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
  • Institut für Anorganische Chemie der Universität Frankfurt, Marie-Curie-Str. 11, D -60439 Frankfurt am Main
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/ Norbert Nagel
  • Institut für Anorganische Chemie der Universität Frankfurt, Marie-Curie-Str. 11, D -60439 Frankfurt am Main
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/ Christian Näther
  • Institut für Anorganische Chemie der Universität Frankfurt, Marie-Curie-Str. 11, D -60439 Frankfurt am Main
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Published Online: 2014-06-02 | DOI: https://doi.org/10.1515/znb-1998-1201

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.

Keywords: Sulfonamides; Crystal Structure; N,N′-Ditosyl-p-phenylendiamine; Density Functional Theory Calculations

About the article

Received: 1998-08-19

Published Online: 2014-06-02

Published in Print: 1998-12-01


Citation Information: Zeitschrift für Naturforschung B, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-1998-1201.

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