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Investigation of aromatic heterocycles

XVII. Peculiarities of the structures of compounds of the dehydro-1,2,3-benzodithiazolium chloride series

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Abstract

The PMR spectra of a number of 1,2,3-dithiazolium chloride derivatives were examined from the point of view of the peculiarities of the structures of these compounds. In deuterosulfuric acid the investigated compounds dissociate completely into ions, and the organic part of the molecule bears a single positive charge. Different variants of the distribution of this charge in the heteroring of the cation were analyzed, and it was established that it is predominantly concentrated on the sulfur atom bonded directly to the benzoid ring. A tendency for delocalization of the positive charge over other atoms of the heteroring was also noted. On the whole, the benzoid ring is distinguished by disruption of the uniformity of bonds according to the quinoid type, which, however, does not lead to a total loss of the aromatic character.

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    Z. V. Todres, B. Kh. Strelets & L. S. Éfros

Authors
  1. Z. V. Todres
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  2. B. Kh. Strelets
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  3. L. S. Éfros
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Additional information

See [1] for communication XVI.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1043–1047, August, 1971.

We sincerely thank É. I. Fedin for his detailed discussions of the results and for his calculations, the results of which are presented in Table 2.

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Todres, Z.V., Strelets, B.K. & Éfros, L.S. Investigation of aromatic heterocycles. Chem Heterocycl Compd 7, 977–980 (1971). https://doi.org/10.1007/BF00477375

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  • DOI: https://doi.org/10.1007/BF00477375

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