166986-23-8Relevant academic research and scientific papers
Concerted bimolecular substitution reactions of anilino thioethers
Eldin, Sherif,Jencks, William P.
, p. 9415 - 9418 (2007/10/03)
The anilino thioethers, 3-NO2-C6H4N(CH3)CH 2SC6H4-2-COO- (1) and 4-NO2-C6H4N(CH3)CH 2SC6H4-2-COO- (2) undergo concerted bimolecular nucleophilic substitution (ANDN) with nucleophilic reagents in aqueous solution at 25 °C that is enforced by the absence of a significant lifetime for the corresponding iminium ion?-SAr intermediates. Electron donation from the aniline nitrogen atom provides assistance to the nucleophilic reaction and results in a dissociative character for the transition state of the reaction. A Swain-Scott correlation with s ≈ 0.4 indicates an early transition state for bond formation, with a low sensitivity of the nucleophilic reaction toward the attacking nucleophile.
Lifetimes of iminium ions in aqueous solution
Eldin, Sherif,Jencks, William P.
, p. 4851 - 4857 (2007/10/02)
Iminium cations have been generated in aqueous solution from the solvolysis of anilinothioethers ArN-(CH3)CH2SR at 25 °C. Common ion inhibition of the solvolysis of anilinothioethers was observed when the thiolate anion leaving group
