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Occurrence and Mechanisms of Aromatic Nucleophilic
The Benzyne or EliminationAddition Mechanism
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4-position A. J. Parker acid activating power addition-elimination aliphatic amines anionic aprotic solvents aromatic aromatic SN reactions aryl aryne B. A. Bolto benzene benzenoid bond calculations catalysis cation Chapter Chem Chim chlorine chlorobenzene co-workers compared conjugative delocalisation diazonium difference dipolar discussed displacement electron electron-releasing electron-withdrawing electronegativity electrophilic entropy EtOH favourable fluorine formation halide halogen heavy nucleophiles heterocyclic hydrogen hydrogen-bonding intermediate complex ion in methanol J. D. Roberts J. F. Bunnett kcal kcal-mole-1 kinetic nucleophilicity leaving group MeOH meta methanol methoxide methoxide ion methoxyl Miller and A. J. negative charge neutral nucleophiles nitro group nitrogen nucleophilic substitution p-values piperidine position Potential energy/reaction coordinate protic solvents proton pyridine Rate constant rate ratio rate-limiting Reaction coordinate reactivity order reacts reagent relative salts similar Sn2 mechanism solvation species stabilisation steric effect substituent substituent effects substrate suggested T.St Table thiocyanate tion transition values whereas