A variety of long-lived carbocations containing the 4-SF5-phenyl group have been characterized. The �SF5 substituent is a relatively novel electron withdrawing substituent, more electronegative than �CF3, and is used to probe for unusual electron delocalization. Nonclassical carbocations thus substituted with the phenyl-SF5 substituent demonstrate deviations from linearity when Hammett parameter (s+) is plotted vs. 13C NMR shifts of the carbocationic center. Plotting the experimentally derived 13C NMR shifts vs. s+ of classical 4-phenyl-X substituted carbocations also provides a novel method of accurately back-calculating the s+ parameter of the �SF5 substituent.

Studies on long-lived carbocations containing the 4-SF<sub>5</sub>-phenyl moiety

248th National Meeting (2014)

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Studies on long-lived carbocations containing the 4-SF5-phenyl moiety

Studies on long-lived carbocations containing the 4-SF₅-phenyl moiety