Study of the Aniline and Acetone Condensation Reaction under Electrospray Ionization Conditions

The present paper deals with the study of condensation reaction of aniline with acetone under electrospray ionization (ESI) conditions . An experimental setup is described for conducting reactions under ESI conditions with a possibility of the accumulation of reaction products. The aniline and acetone condensation products were analyzed by gas chromatography–mass spectrometry. Spraying this mixture with high concentration of formic acid, results in the formation of N-phenylformamide, N,N'-diphenylmethaneimidamide, and 1,2-dihydro-2,2,4-trimethylquinoline; the last one is the only product of the reaction of aniline with acetone. Thus, the Schiff base formation reaction radically changes its direction. The results obtained using the proposed experimental setup open up new prospects both for studying chemical reactions in charged microdroplets and for the use of ESI as a preparative method for the synthesis of organic compounds.