Journal article
Letter: Silver mediated ester bond formation in the gas phase: substrate structure is important
George N Khairallah, Tom Waters, Richard AJ O'Hair
EUROPEAN JOURNAL OF MASS SPECTROMETRY | SAGE PUBLICATIONS LTD | Published : 2007
DOI: 10.1255/ejms.888
Abstract
The silver acetate cation CH(3)CO(2)Ag(2)(+) reacted with allyl iodide via C-O bond coupling to produce Ag(2)I(+) 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 CH(3)CO(2)Ag(2)(+).