6533b82bfe1ef96bd128e31c

RESEARCH PRODUCT

Mass spectrometric studies of benzoxazine resorcarenes

Kari RissanenKati HakalaJari M. J. NuutinenThomas StraubPirjo Vainiotalo

subject

Spectrometry Mass Electrospray IonizationElectrosprayChemistryOrganic ChemistryAnalytical chemistryResorcinolsMass spectrometryAlkali metalFourier transform ion cyclotron resonanceAnalytical ChemistryIonFragmentation (mass spectrometry)Spectrometry Mass Matrix-Assisted Laser Desorption-IonizationReagentOxazinesMoleculeSpectroscopy

description

Eleven differently substituted 3,4-dihydro-2H-1,3-benzoxazine resorcarenes were studied by electrospray ionisation (ESI) and matrix-assisted laser desorption/ionisation (MALDI) mass spectrometry, using Fourier transform ion cyclotron resonance (FT-ICR) and time-of-flight (TOF) mass spectrometers, respectively. Under ESI conditions it was possible to transfer the intact resorcarenes from solution to the gas phase, yielding [M + H]+ and [M + 2H]+ ions as the main ions observed. Energy increase of the ions induced ready decomposition through successive eliminations of four CH2NR groups. Ion-molecule reactions showed that the ionising proton was situated somewhere inside the molecule and could not be reached with neutral reagent gases. In the host-guest complexation experiments, the benzoxazine resorcarenes studied turned out to be poor hosts for alkali metal and ammonium ions. In MALDI experiments, 2,5-dihydroxybenzoic acid proved to be the best matrix for these compounds. However, the intensity of the [M + H]+ ions was low for all compounds, and extensive fragmentation with consecutive elimination of CH2NR groups was observed. Copyright © 2002 John Wiley & Sons, Ltd.

yearjournalcountryeditionlanguage
2002-08-31Rapid Communications in Mass Spectrometry
https://doi.org/10.1002/rcm.770