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Letter: Silver mediated ester bond formation in the gas phase: substrate
structure is important George N. Khairallah,a,b Tom Watersa,b and Richard A.J.
O'Hair*,a–c
aSchool of Chemistry, University of Melbourne, Victoria 3010, Australia. E-mail:
rohair@unimelb.edu.au
bBio21 Institute of Molecular Science and Biotechnology, The University of Melbourne, Victoria 3010, Australia
cARC
Centre of Excellence in Free Radical Chemistry and Biotechnology
ABSTRACT:
The silver acetate cation CH3CO2Ag2+ reacted
with allyl iodide via C–O bond coupling to produce Ag2I+ and allyl acetate, but only underwent adduct formation with methyl iodide,
highlighting the importance of substrate on reactivity. DFT calculations predicted the reaction with allyl iodide to be exothermic by 0.48 eV, and suggested that intermediates in
the reaction benefit from multiple interactions between the allyl and iodide moieties of allyl iodide and the two silver atoms in
CH3CO2Ag2+.
Keywords:
silver acetate cluster cations, silver iodide cluster cations, electrospray, tandem mass spectrometry, gas-
phase ion–molecule reactions, allyl iodide, methyl iodide, C–I bond activation, C–O bond formation, DFT calculations
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