Abstract
Nucleophilic aromatic substitution reactions of 4-chloroquinazoline toward aniline and hydrazine were used as a model system to experimentally show that a substrate bearing heteroatoms on the aromatic ring as substituent is able to establish intramolecular hydrogen bond which may be activated by the reaction media and/or the nature of the nucleophile.
Highlights
The electrophilicity (ω+) and nucleophilicity (ω−) concepts (Ingold, 1929, 1933, 1934) are related to electron-deficient and electron-rich species (Jaramillo et al, 2006)
The solvent effects usually are studied in aromatic nucleophilic substitution (SNAr) reactions, because the reaction media involves the stabilization of species associated to the Potential Energy Surface (PES) such as: electrophile/nucleophile (E+/Nu−) pair, transition state (TS) and intermediate structures, respectively (Ormazábal-Toledo et al, 2013c; Gazitúa et al, 2014; Alarcón-Espósito et al, 2015, 2016, 2017)
The reactions have been studied because the electrophile bears heteroatoms on the aromatic ring as substituent able to establish intramolecular hydrogen bond (HB) that may be activated by solvation or by the nucleophile
Summary
The electrophilicity (ω+) and nucleophilicity (ω−) concepts (Ingold, 1929, 1933, 1934) are related to electron-deficient (electrophile) and electron-rich (nucleophile) species (Jaramillo et al, 2006). The solvent effects usually are studied in aromatic nucleophilic substitution (SNAr) reactions, because the reaction media involves the stabilization of species associated to the Potential Energy Surface (PES) such as: electrophile/nucleophile (E+/Nu−) pair, transition state (TS) and intermediate structures, respectively (Ormazábal-Toledo et al, 2013c; Gazitúa et al, 2014; Alarcón-Espósito et al, 2015, 2016, 2017).
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