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

Ibon Alkorta, Luis Miguel Azofra Mesa, Goar Sanchez-Sanz, Jose Elguero

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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 sixmembered 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.
Original languageEnglish
Pages (from-to)1245 - 1252
Number of pages8
JournalStructural Chemistry
Issue number4
Publication statusPublished - 2012
Externally publishedYes

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