10242-29-2Relevant academic research and scientific papers
Kinetics of the reaction of phenyl picrates with phenoxide ions in water. Concerted or stepwise?
Crampton, Michael R.,Robotham, Ian A.
, p. 1084 - 1089 (2014/01/06)
A kinetic study is reported of the exchange reactions of substituted phenoxide ions with some ring-substituted 2,4,6-trinitrophenyl ethers in water. The βronsted diagrams formed by plotting log k, where k is the second-order rate constant for reaction, ve
Leaving group effects on the mechanism of aromatic nucleophilic substitution (SnAr) reactions of some phenyl 2,4,6-trinitrophenyl ethers with aniline in acetonitrile
Crampton, Michael R.,Emokpae, Thomas A.,Howard, Judith A.K.,Isanbor, Chukwuemeka,Mondal, Raju
, p. 65 - 70 (2007/10/03)
Kinetic studies are reported for the reactions with aniline in acetonitrile of a series of X-phenyl 2,4,6trinitrophenyl ethers [X = H, 2-, 3-, 4-CH3,2,4-, 2,6-(CH3)2,2-, 3-, 4-NO 2,2,4-, 2,6-(NO2)2]. X-ray crystal structures for X = H, 2,6-(CH3)2 and 2,6-(NO2) 2 are reported and provide evidence for steric crowding around the 1-position of these molecules. Nevertheless, the kinetic data show that increasing substitution does not sterically inhibit nucleophilic attack by aniline and an 'early' transition state is likely. In general, the reactions are base catalysed; interpreted as rate-limiting deprotonation of the zwitterionic intermediates. Only with the dinitro derivatives is an uncatalysed reaction involving intramolecular proton transfer observed and when X = 2,6-(NO2)2 this pathway takes all the reaction flux. Copyright
