The vinyl cation is a carbocation with the positive charge on an alkene carbon. Its empirical formula is C
2H+
3. More generally, a vinylic cation is any disubstituted carbon, where the carbon bearing the positive charge is part of a double bond and is sp hybridized. In the chemical literature, substituted vinylic cations are often referred to as vinyl cations, and understood to refer to the broad class rather than the C
2H+
3 variant alone. The vinyl cation is one of the main types of reactive intermediates involving a non-tetrahedrally coordinated carbon atom, and is necessary to explain a wide variety of observed reactivity trends. Vinyl cations are observed as reactive intermediates in solvolysis reactions,[1][2] as well during electrophilic addition to alkynes,[3] for example, through protonation of an alkyne by a strong acid. As expected from its sp hybridization, the vinyl cation prefers a linear geometry. Compounds related to the vinyl cation include allylic carbocations and benzylic carbocations, as well as aryl carbocations.
- ^ Okuyama, T. (2002). "Solvolysis of Vinyl Iodonium Salts. New Insights into Vinyl Cation Intermediates". Acc. Chem. Res. 35 (1): 12. doi:10.1021/ar0100374.
- ^ Gronheid, R (2001). "Thermal and Photochemical Solvolysis of (E)- and (Z)-2-Phenyl-1-Propenyl(phenyl)iodonium Tetrafluoroborate: Benzenium and Primary Vinylic Cation Intermediates". J. Am. Chem. Soc. 123 (36): 8760. doi:10.1021/ja010861n.
- ^ Walkinshaw, Andrew J.; Xu, Wenshu; Suero, Marcos G.; Gaunt, Matthew J. (2013). "Copper-Catalyzed Carboarylation of Alkynes via Vinyl Cations". Journal of the American Chemical Society. 135 (34): 12532–12535. doi:10.1021/ja405972h. PMID 23947578.
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