Conclusions
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1.
There is virtually no p, it-interaction of the sulfur atom with the aromatic ring in sterically hindered 1-alkylthio-2,4,6-trimethylbenzene due to the close-to-orthogonal effective conformation of these molecules.
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2.
The occupancy of the close-to-planar conformation in 1-alkylthio-4-methylbenzenes decreases with increasing bulk of the -SAlk groups, while the occupancy of the nonplanar conformer increases. As a consequence, the13C NMR spectra display changes related to breakdown of the p, π-interaction in the thiobenzene fragment (steric breakdown of conjugation).
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For previous communication, see [1].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1032–1036, May, 1988.
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Dolenko, G.N., Bzhezovskii, V.M. & Aliev, I.A. Conjugation effects. 27. Analysis of the13C NMR spectra and SKβ X-ray fluorescence spectra of 1-alkylthio-2,4,6-trimethylbenzenes. Russ Chem Bull 37, 900–904 (1988). https://doi.org/10.1007/BF00957056
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DOI: https://doi.org/10.1007/BF00957056