Structural Chemistry

, Volume 23, Issue 4, pp 1245–1252 | Cite as

A theoretical study of six-membered rings containing the –N=S–S=N– motif

  • Ibon Alkorta
  • Luis Miguel Azofra
  • Goar Sánchez-Sanz
  • José Elguero
Original Research

Abstract

The sulfur electronic structure allows for the existence of hypervalent molecules that were discussed as early as 1939 by Schomaker and Pauling. In the present paper, we report a theoretical study of three hypothetical possible six-membered rings that contain the –N=S–S=N– motif carried out at the MP2/aug-cc-pVDZ level. Three minima have been found, of which two of them are six-membered rings with all covalent bonds. Since they do not have a planar structure, we have calculated the aromaticity index NICS through the symmetry axis perpendicular to the mid-plane and at various points in space. Benzene, cyclohexane, and 1,2,5-thiadiazole have served as points of comparison.

Keywords

NSSN motif MP2 aug-cc-pVDZ Heterocycles Aromaticity NICS 

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Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Ibon Alkorta
    • 1
  • Luis Miguel Azofra
    • 1
  • Goar Sánchez-Sanz
    • 1
  • José Elguero
    • 1
  1. 1.Instituto de Química Médica, CSICMadridSpain

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