Solvents effects on aromatic nucleophilic substitutions. Part 5. Kinetics of the reactions of 1-fluoro-2,4-dinitrobenzene with piperidine in aprotic solvents

Isotope effects for fluorine‐18 and carbon‐11 in the study of reaction mechanisms

“…THF. 16 The resulting leaving group KIE when changing the solvent is therefore interesting; it also gives further evidence that the observed KIE is real and not an artefact.…”

Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a SNAr Reaction Toward Trends in Reaction Pathways

“…The nucleophilic aromatic substitution (S N Ar) reactions have been the object of several studies, especially in solvation analysis and solvent effects studies in water, conventional organic solvents (COS), ionic liquids (ILs), and mixtures of them (Nudelman et al, 1987 ; Newington et al, 2007 ; D'Anna et al, 2010 ; Park and Lee, 2010 ; Alarcón-Espósito et al, 2015 , 2016 , 2017 ; Marullo et al, 2016 ; Sánchez et al, 2018a , b ). However, only in the last time these reactions have been investigated systematically in order to acquire knowledge about the rate determining step (RDS) on the reaction mechanism based on Brönsted type-plots (Um et al, 2007 ; Ormazábal-Toledo et al, 2013a , b ; Gallardo-Fuentes et al, 2014 ; Gazitúa et al, 2014 ).…”

A Greener and Efficient Method for Nucleophilic Aromatic Substitution of Nitrogen-Containing Fused Heterocycles

“…In view of our interest in the development of green chemistry procedures [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 ], we report herein the use of PEG400 as an efficient medium for nucleophilic aromatic substitution (S N Ar) of some nitrogen-containing fused heterocycles with various amines. S N Ar involving amines have been carried out and studied in conventional organic solvents [ 35 , 36 , 37 , 38 , 39 ] but also in non-volatile alternative media such as ionic liquids [ 40 , 41 , 42 , 43 , 44 ], but, to the best of our knowledge, this reaction has never been reported using PEG as the solvent.…”