Gas-Phase studies on the reactivity and formation of para-benzynes and carbon-nitrogen (CN) ortho-benzynes in a fourier transform ion cyclotron resonance (FT-ICR) mass spectrometer

For over a century, the benzynes have been the focus of numerous theoretical and experimental studies. ortho-Benzynes, the most studied benzynes, were identified long ago as the key reaction intermediates of several organic reactions, including nucleophilic aromatic substitution and 1,3-cycloaddition. More recently, substituted para-benzynes have been suggested to act as the biologically-active intermediates of the enediyne antitumor antibiotics. This finding has led to an increased interest in the properties of benzynes. However, their intrinsic chemical properties are still largely unknown. Utilizing the distonic ion approach, the reactivities of para-benzynes and carbon-nitrogen (CN) ortho-benzynes were examined in a dual-cell Fourier transform ion cyclotron resonance mass spectrometer (FT-ICR) in order to gain further insight on the chemical properties that control them