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- W1976151503 abstract "By means of low-temperature NMR spectra, it is demonstrated that dimesityl sulfine (Mes2C=SO) adopts in solution the same chiral propeller conformation (C1 symmetry) determined by X-ray diffraction in the crystalline state. With the help of MM calculations, it has been also shown that a correlated rotation (cog wheel effect) of the two mesityl rings reverses the molecular helicity according to an enantiomerization process entailing a one-ring flip pathway with delta G++ = 5.9 kcal mol-1 and a two-ring flip pathway with delta G++ = 13.8 kcal mol-1. On the contrary the Z- and E-isomers of mesityl phenyl sulfine (MesPhC=SO) adopt essentially achiral conformations (Cs symmetry), having the Ph-CSO rotation barriers equal to 5.2 and 5.8 kcal mol-1, respectively, and the mesityl-CSO rotation barriers equal to 21.3 and 15.1 kcal mol-1, respectively." @default.
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- W1976151503 date "2001-01-23" @default.
- W1976151503 modified "2023-10-18" @default.
- W1976151503 title "Conformational Studies by Dynamic NMR. 79.<sup>1</sup> Dimesityl Sulfine Revisited: Detection of the Helical Antipodes and Determination of Their Enantiomerization Pathways" @default.
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- W1976151503 doi "https://doi.org/10.1021/jo001408h" @default.
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