COMPUTATIONAL STUDY OF CONCERTED REACTION PATHWAYS FOR N-ALKYLANINE TRANSFORMATION TO ANILINE IN ACID MEDIA AND UNDER GAS PHASE

Experimentally the transformation of N-alkylaniline to aniline is assumed to proceed by SN2 reaction pathway. New concerted reaction pathway was proposed. These concerted reaction pathways were studied computationally and compared using different alkyl substituents (methyl and isopropyl). The computational calculation was carried out with Density Functional Theory using B3LYP (Becke-style 3-Parameter Density Functional Theory, that use Lee-Yang-Parr correlation functional) and 6-311++G (d, p) basis set. The reaction pathways were followed and verified with Intrinsic Reaction Coordinate (IRC). It was found that, in accordance with the experimental assumption, SN2 reaction pathway was the choice of the transformation.