Abstract
Stereoelectronic effects in thianes and thiane‐derived sulfoxides, sulfones, sulfilimines, and sulfoximines were investigated by measuring1JC,Hcoupling constants and by identification of normal and reversed Perlin effects, i.e., of differences in the coupling constants for equatorial and axial C–H bonds in the methylene groups of six‐membered rings. The Perlin effects were correlated with results from natural bond orbital (NBO) analyses. NMR experiments were performed with conformationally restricted dimethyl‐ ortert‐butyl‐substituted derivatives, while the parent compounds were used for calculations. It turned out that the coupling constants are not only strongly influenced by stereoelectronic interactions with antiperiplanar C–H, C–C, C–O, and C–N bonds, but by the s character of the respective C–H bonds' carbon orbital as well.
Highlights
The stability, conformation, and reactivity, as well as various physical and in particular spectroscopic properties are significantly influenced by stereoelectronic effects.[1]
In this paper we examine 1JC,H coupling constants in thianes and in thiane-derived sulfoxides, sulfones, sulfilimines, and sulfoximines by experimental and by quantum chemical methods
Perlin effects observed in thiane-derived compounds can be qualitatively explained with the data obtained from natural bond orbital (NBO) analyses, it turned out that no direct correlation between coupling constants and calculated resonance energies is possible
Summary
The stability, conformation, and reactivity, as well as various physical and in particular spectroscopic properties are significantly influenced by stereoelectronic effects.[1]. Perlin effects observed in thiane-derived compounds can be qualitatively explained with the data obtained from NBO analyses, it turned out that no direct correlation between coupling constants and calculated resonance energies is possible.
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