32024-99-0Relevant articles and documents
Kinetic studies of σ-adduct formation and nucleophilic substitution in the reactions of ethyl 2,4,6-trinitrophenyl ether, some phenyl 2,4,6- trinitrophenyl ethers, and phenyl 2,4-dinitronaphthyl ether with aniline in dimethyl sulfoxide
Crampton, Michael R.,Robotham, Ian A.
, p. 627 - 634 (1998)
The reaction of ethyl 2,4,6-trinitrophenyl ether with aniline in dimethyl sulfoxide containing Dabco occurs in two stages. The first gives 5, the σ-adduct intermediate on the substitution pathway, which has been identified spectroscopically. The second yields 2,4,6-trinitrodiphenylamine, the substitution product. Kinetic studies show that proton transfer is rate limiting both in the formation of the intermediate and in its subsequent acid-catalysed decomposition. Phenoxide is a considerably better leaving group than ethoxide and the substitution reactions of phenyl 2,4,6- trinitrophenyl ethers and phenyl 2,4-dinitronaphthyl ether with aniline in DMSO occur without the accumulation of intermediates. The kinetics indicate both uncatalysed and base-catalysed pathways. The kinetic and equilibrium data for reaction of the ethyl and phenyl ethers are compared with data for σ-adduct formation from 1,3,5-trinitrobenzene and aniline.
A COMPARATIVE KINETIC INVESTIGATION OF SOME NUCLEOPHILIC AROMATIC DISPLACEMENTS
Kharaba, Mohamed A. H.,Nassar, Ahmad M. G.,Youssef, Abdel-Hamid A.,Faid-Allah, Hassan M.
, p. 1029 - 1034 (2007/10/02)
A comparative kinetic study of the reaction of 1-chloro-2,4-dinitrobenzene, 1-chloro-2,4-dinitronaphthalene, 2-chloro-5-nitropyridine and 2-chloro-3-nitropyridine with phenoxide, 1-naphthoxide and 2-naphthoxide ions was performed in methanol solution.Rate constants at five temperatures and Arrhenius parameters have been determined for all reactions.
