Title |
Reactions of Organic Ions at Ambient Surfaces in a Solvent-Free Environment
|
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Published in |
Journal of the American Society for Mass Spectrometry, January 2012
|
DOI | 10.1007/s13361-012-0337-7 |
Pubmed ID | |
Authors |
Abraham K. Badu-Tawiah, Jobin Cyriac, R. Graham Cooks |
Abstract |
Solvent-free ion/surface chemistry is studied at atmospheric pressure, specifically pyrylium cations, are reacted at ambient surfaces with organic amines to generate pyridinium ions. The dry reagent ions were generated by electrospraying a solution of the organic salt and passing the resulting electrosprayed droplets pneumatically through a heated metal drying tube. The dry ions were then passed through an electric field in air to separate the cations from anions and direct the cations onto a gold substrate coated with an amine. This nontraditional way of manipulating polyatomic ions has provided new chemical insights, for example, the surface reaction involving dry isolated 2,4,6-triphenylpyrylium cations and condensed solid-phase ethanolamine was found to produce the expected N-substituted pyridinium product ion via a pseudobase intermediate in a regiospecific fashion. In solution however, ethanolamine was observed to react through its N-centered and O-centered nucleophilic groups to generate two isomeric products via 2H-pyran intermediates. The O-centered nucleophile reacted less rapidly to give the minor product. The surface reaction product was characterized in situ by surface enhanced Raman spectroscopy, and ex situ using mass spectrometry and H/D exchange, and found to be chemically the same as the major pyridinium solution-phase reaction product. |
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