CHARACTERIZATION BY ELECTROSPRAY TANDEM MASS-SPECTROMETRY OF A NOVEL SERIES OF SYNTHETIC DIFURANIC DIAMINE DIHYDROCHLORIDES CONTAINING THE BIS(5-AMINOMETHYL-2-FURYL) UNIT

Electrospray mass spectrometry has aided the structural characterizati on and differentiation of a novel series of synthetic difuranic diamin e hydrochlorides. As expected, these compounds generally afforded the protonated molecules minus two molecules of HCl to yield the abundant [M+H-2HCl](+) pseudomolecular ions, which are equivalent to the [M+H]( +) ions obtained from the corresponding free difuranic diamine compoun ds. Possible fragmentation routes were first obtained by controlled co llisionally activated dissociation (CAD) initiated by cone-voltage fra gmentation. Low-energy CAD tandem mass spectrometric analyses of the [ M+H-2HCl](+) ions confirmed the characteristic fingerprint patterns ob tained by cone-voltage fragmentation for all the difuranic diamine com pounds investigated. MS/MS product-ion spectra of selected intermediat e fragments provided additional structural data and confirmed the frag mentation routes of their precursor ions. Electrospray mass spectromet ry has been proven to be a specific and very sensitive method for dete ction and characterization of these navel difuranic diamine hydrochlor ides.