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Keywords:

  • gas phase reactions;
  • rearrangement;
  • Smiles reaction;
  • ESI-MS/MS;
  • urea-carbamimidic acid tautomerism

Abstract

The gas-phase rearrangement reactions of compound 1, 2-dimethoxypyrimidinyloxybenzylaminoben- zenedipropylurea, were studied by ESI-MS/MS. The experimental results showed that introduction of dipropylurea moiety into the molecule initiated various interesting gas-phase chemistries and the mechanisms were proposed on the basis of hydrogen/deuterium (H/D) exchange experiments and theoretical computations. Moreover, product 2, the solution-phase rearrangement product of compound 1, was synthesized and its gas-phase chemistries were also studied to support the propos gas-phase rearrangement reactions of compound 1.