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Comparison of cation binding affinities of quinones

Authors
Journal
International Journal of Mass Spectrometry and Ion Processes
0168-1176
Publisher
Elsevier
Publication Date
Volume
155
Issue
3
Identifiers
DOI: 10.1016/s0168-1176(96)04418-7
Keywords
  • Borinium Ion Affinity
  • Gas-Phase Basicity
  • Ligand Exchange
  • Quadrupole Ion Trap
  • Quinone

Abstract

Abstract The relative gas-phase basicity scale and the relative dimethoxy borinium ion affinity scale of various quinones were determined by the ligand exchange method to investigate the structural factors which influence the binding properties of the quinones. The relative gas-phase basicity scale and dimethoxy borinium ion affinity scale were similar, and were proved to correlate with the extent of favorable functional group interactions and counteractive electron-withdrawing effects of certain substituents. For 1,2-naphthoquinone and lawsone the order of affinities was reversed, presumably because of a secondary hydrogen-bonding interaction active for lawsone that particularly enhanced the stability of its borinium adduct.

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