Kinetic oxygen and hydrogen isotope effects in the hydroxide ion catalized reaction of 2,4-dinitrophenyl phenyl ether with piperidine in aqueous dioxane

✍ Scribed by C.R. Hart; A.N. Bourns

• Publisher: Elsevier Science
• Year: 1966
• Tongue: French
• Weight: 319 KB
• Volume: 7
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)99902-2

✦ Synopsis

The intermediate cunplex mechanism for aromatic nucleophilic Sub&itution reactions of activated canpounde is indicated by a variety of evidence much of which has been provided by the work of Bunnett and coworkers (1). The concerted SN2 mechanism has continued to have its proponents, however, particularly for the reaction of halonitrobenzenes with amines in hydroxylic solvents (2). Strongest support for the intermediate complex mechanism is found in Bunnett's recent study (3) of the kinetic form of the base catalysis of the reaction of 2,Ldinitrophenyl phenyl ether with piperidine in aqueous dioxane. The observation that the second order rate constant, 4, for the foneation of 2,44initrophenylpiperidine shows a curvilinear dependence on hydroxide ion concentration is in accord with the scheme of eq. [I],