The sensitivity of carbon and nitrogen atoms in two structures of 2- benzylaminopyridine (I,II) and its cations (III,IV) to an electrophilic agent attack were investigated in order to determine which are responsible for its 5-benzyl and AT-benzyl derivative formation in the reaction with benzyl cation. For predicting the most sensitive centres, net atomic charges and HOMO electron density plots were calculated by the MNDO-method, as well as the Fukui function (FF) indices and relaxed chemical potentials of atoms-in- molecules (AIM) within a charge sensitivity (CS) scheme. The analysis indicates that only in structures I and II the sensitivity of the carbon and nitrogen atoms explains the experimental facts. The analysis also shows that 2-benzylaminopyridine cations (m and IV) did not participate in the 5-benzyl and IV-benzyl derivatives of 2-benzylaminopyridine formation. Their presence in the reaction mixture influenced the formation and stabilization of the benzyl cation
