Journal of the American Chemical Society p. 289 - 295 (1981)
Update date:2022-08-30
Topics:
Hashmall, J. A.
Horak, V.
Khoo, L. E.
Quicksall, C. O.
Sun, M. K.
Molecular structures of 5-methyldibenzothiophenium tetrafluoroborate (I), 1-methylnaphtho<2,3-b>thiophenium tetrafluoroborate (II), and dibenzothiophene 5-oxide (III) were determined by X-ray diffraction.The effect of increase of coordination at the sulfur atom (with respect to sulfur atom in thiophene-like molecules) was evaluated by examining the planarity of the structure, stereochemistry at the sulfur atom, CS bond distances, and the CC bonds alternation in the carbon atom framework.The experimental reults parallel the results of MNDO semiempirical calculations of model species, i.e., thiophene (IV), the S-methylthiophenium ion (V), and thiophene S-oxide (VI).The changes of aromaticity of the thiophene-like molecules resulting from the substitution at the sulfur atom are discussed in terms of the perturbation theory by using HMO models.
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