Multiple hydrogen/lithium interconversions at the same benzene nucleus: Two at the most

M Schlosser, L Guio, F Leroux

Index: Schlosser; Guio; Leroux Journal of the American Chemical Society, 2001 , vol. 123, # 16 p. 3822 - 3823

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Citation Number: 32

Abstract

Every first-year student is advised not to draw formulas carrying two like charges in close vicinity. Electrostatic repulsion, so goes the argument, would make such structures energetically exorbitant and hence unrealistic. This plausible rule of thumb is confirmed by recent computational work at the MP2, MP4, and B3LYP levels of theory. Proton abstraction from a “naked” phenyl anion by another phenyl anion is a highly endothermal process, ...