Molecular Orbital Study of the Nitrosation of Active Methyl and Methylene Groups of Pyridine and Pyrimidine Derivatives

The reactivity of active methyl and methylene groups of nitrogen-containing hetero-aromatics with alkyl nitrite in the presence of an amide ion is discussed in terms of the charge transfer ability (CTA) values according to CNDO/2 as well as PPP calculations. Intermolecular perturbation energy calculation was also applied to interpret this nitrosation. The experimental results of nitrosation can be reasonably well interpreted in terms of the CTA values in the deprotonation step of this reaction. The binding energies of methylheteroaromatics are also discussed.