Aromatic Nucleophilic Substitution, Volume 8

1-halogeno-2,4-dinitrobenzenes 4-position A. J. PARKER acid addition-elimination aliphatic amines anionic aprotic solvents aromatic aromatic SN reactions aryl atom B. A. BOLTO benzene benzenoid bond calculations carbon catalysis cation Chapter Chem Chim chlorine chlorobenzene co-workers compared conjugative delocalisation diazonium difference discussed displacement electron electron-withdrawing electronegativity electrophilic energy/reaction coordinate profile entropy EtOH favourable fluorine formation halide halogen heavy nucleophiles heterocyclic hydrogen hydrogen-bonding I.St intermediate complex iodide J. D. ROBERTS J. F. BUNNETT k₂ kcal mole¹ kinetic nucleophilicity leaving group meta methanol methoxide methoxide ion methoxyl MILLER AND A. J. mobility mole-¹ 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 stabilisation steric effect substituent substituent effects substrate suggested Table thiocyanate transition values whereas