Abstract: X-Ray diffraction examination and MNDO calculations have shown that 1,3,2-benzodithiazolium chloride (I) is ionic, with a planar heteroaromatic 10π-electron cation. The π-MO of the cation (I) is isolobal with the p-MO of benzo-2,1,3-thiadiazole. In the cation of (I), as in the latter compound, the p-AO of nitrogen and sulfur contribute for the most part to π-MO of differing symmetry (b1 and a2, respectively). This has the consequence that although both nitrogen and sulfur participate in the formation of a single π-system in the thiazolium cation of (I), there is virtually no π-bonding between them. Generally speaking, the π-MO of the (I) cation shows a tendency to localization on separate molecular fragments. The charge on the cation is localized at the SNS group, and the five-membered ring is strongly polarized. These features all reduce the heteroaromaticity of the system. © 1991 Plenum Publishing Corporation.

Cite: Zibarev A.V. , Bagryanskaya I.Y. , Latilov Y.V. , Shchegoleva L.N. , Dolenko G.N. , Furin G.G.
Crystal, molecular, and π-electronic structure of 1,3,2-benzodithiazolium chloride
Chemistry of Heterocyclic Compounds. 1990. V.26. N12. P.1399-1404. DOI: 10.1007/BF00473972 Scopus РИНЦ

Dates:

Published print:

Dec 1, 1990

Identifiers:

Scopus	2-s2.0-34249928190
Elibrary	30832117
OpenAlex	W2013429186

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