72212-34-1Relevant academic research and scientific papers
NUCLEOPHILIC SUBSTITUTION REACTIONS OF CUMYL CHLORIDES IN METHANOL
Lee, Ikchoon,Koh, Han Joong,Hong, Sung Nam,Lee, Bon-Su
, p. 347 - 352 (2007/10/02)
Nucleophilic substitution reactions of cumyl chlorides with anilines in methanol have been investigated.Large negative ρY+ values in methanol and weak chloride common ion rate depression support a mechanism in which a preformed benzylic-type carbocation intermediate reacts with the solvent and the added nucleophile, aniline.All positive ρX (ρnuc) values observed and the estimated non-interactive point, ?Y+ = 0.72, strongly suggest that deprotonation of a mobile proton from the nucleophile occurs during the reaction.Fair linear correlation is exhibited for the plot of stability of carbocation, as expressed by the enthalpy of cation formation (AM1), and ?Y+, indicating that the thermodynamic driving force is nearly compensated for by the intrinsic barrier.
