Activation of Electrophile/Nucleophile Pair by a Nucleophilic and Electrophilic Solvation in a S(N)Ar Reaction

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.