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• W2951475574 abstract "Abstract This overview summerizes the most important aspects of our present day knowledge about the title species. The material is presented in two sections; the first one reminds salient physico-chemical results related to the stabilization of carbenium ions by selenium moieties and the second one gives examples of the synthetic usefullness of these electrophiles. Gas phase proton affinity measurements complemented by ab initio MO calculations revealed that the intrinsic carbocation stabilizing ability of the Group 16 elements decreases from oxygen to tellurium. However, this ability is not connected in a straightforward manner to the dispersion of the cation's positive charge. The latter is the largest for the most stable species, i.e. oxocarbenium ions, and it decreases downwards in Group 16. Therefore, coulombic (i.e. electrostatic) factors must play a significant role in the overall stabilization. It follows that oxocarbenium should be considered as hard electrophiles undergoing rapid charge contolled reactions with hard nucleophiles, whereas seleno- and tellurocarbenium ions are soft electrophiles giving rise to slow reactions with the same hard nucleophiles. The ability of a series of selenocarbenium ion precursors to undergo useful inter- and intramolecular C, C bond forming reactions is illustrated." @default.
• W2951475574 created "2019-06-27" @default.
• W2951475574 creator A5039144251 @default.
• W2951475574 date "2001-04-01" @default.
• W2951475574 modified "2023-09-27" @default.
• W2951475574 title "Twenty Years of Chemistry of Selenium Stabilized Carbenium Ions" @default.
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• W2951475574 doi "https://doi.org/10.1080/10426500108046628" @default.
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