The microcosmic reaction mechanism of 2-(fluorohexanamidyl)-benzaldehyde and ammonia were studied by density functional theory. The geometries of the reactants, transition states, intermediates and products were optimized at the B3LYP/6-31G* level. Vibration analysis was carried out to confirm the transition state structure, and the intrinsic reaction coordinate (IRC) method was performed to search the reaction path. In addition, atoms in molecules (AIM) theories have been used to discuss bond natures.Feasible reaction pathways were investigated in this study. Analysis indicate that the reaction Re→TS1→IM1→TS2→IM2→TS3→IM3→TS4→IM7→TS11→IM9→IS12→IM10→ TS13→IM11→TS14→P1 is the main pathway, the activation energy of which is the lowest. The dominant product predicted theoretically is in agreement with the results in the experiment. The reaction in ethanol solution has been investigated at the same level with SCRF (PCM) method, and the results show that the energy of each compound is lower than that in the gas phase. The solvent effects enhance the energy barrier to some extent.

Key words: 2-(fluorohexanamidyl)-benzaldehyde, 3-(1-iminofluoroalkyl)-1H-quinolin