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- W2001957275 abstract "Relatively few structure determinations of α-sulphonyl stabilized carbanions have been reported. The salient features of these are summarized and discussed in the light of the X-ray crystal structures of the potassium salt from bis(methylsulfonyl)-3-(2,6-dimethoxypyridyl)sulfonylmethane (5), the carbon acid bis(methylsulphonyl-4-(1,3-dimethoxyphenyl)sulphonylmethane (6), the triethylammonium salt of 2-methylsulphonyl-2-phenylthio-1-(3-pyridyl)-1-ethanone (7), the carbon acid 2-methyl-sulphonyl-2-phenylthio-1-phenylethanone (8), and its triethylammonium salt (9). Results of these structure determinations show that the α-sulphonyl carbanion has a significantly shorter − C—SO 2 bond distance than the free sulphone, but that the S—O bond distances are essentially unchanged. The coordination about the carbanionic carbon atoms is planar; these atoms can be described as interacting with the sulphur atoms in an ylid-like manner, with a barrier to rotation about the − C—SO 2 bond. The sulphonyl oxygen atoms do interact to a significant degree with the counterion, but there is no close contact between the counterion and the carbanionic carbon atom. A comparison of the structures of 6 and 5, or of 8 and 9, permits an assessment to be made concerning the stereoelectronics of deprotonation reactions on carbon atoms adjacent to sulphones." @default.
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- W2001957275 date "1987-06-01" @default.
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- W2001957275 title "The structures of some sulphur-stabilized carbanions and stereoelectronic requirements for the formation of α-sulphonyl carbanions" @default.
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- W2001957275 doi "https://doi.org/10.1139/v87-238" @default.
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