Site activation effects promoted by intramolecular hydrogen bond interactions in SNAr reactions
Journal
RSC Adv.
ISSN
2046-2069
Date Issued
2014
Author(s)
Sebastián Gallardo-Fuentes
Ricardo A. Tapia
Renato Contreras
Type
Resource Types::text::journal::journal article
URL Institutional Repository
Abstract
<p>The nucleophilic aromatic substitution reaction of benzohydrazide derivatives towards 2-chloro-5-nitropyrimidine is used as model system to experimentally and theoretically show that intramolecular hydrogen-bond formation operates as a perturbation that elicits a dual response at the reaction center of the transition state (TS) structure.</p>
Subjects
aromatic nucleophilic-substitution
;
markovnikov regioselectivity rule
;
secondary-amines
;
solvent
;
electrophilicity
;
functionals
;
potentials
;
reactivity
;
molecules
;
model