Abstract
The mass spectrometric behavior of lithiated derivatives of 2,5-disubstituted-1,3,4-oxadiazoles has confirmed the skeletal rearrangement presented earlier for protonated derivatives. In the case of [M + H]+ ions the loss of isocyanic acid was observed and for [M + Li]+ ions the loss of lithium isocyanate occurred. On the other hand, benzoyl ions [RCO]+ were formed from [M + H]+ ions, but not from [M + Li]+ ions. Formation of benzoyl ions was in agreement with the differences between bond orders calculated for [M+H]+ ions and neutral molecules. From [M + Li]+ ions the [RCNLi]+ fragment ions were formed, but the formation of [RCNH]+ fragment ions from [M + H]+ ions was not observed. This result can be explained on the basis of theoretically calculated stabilities of these fragment ions, since the calculated heats of formation of [RCNLi]+ ions were found to be substantially lower than those of the respective [RCNH]+ ions.
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Published online February 27, 2003
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Frański, R., Eitner, K., Schroeder, G. et al. Mass spectrometric study of some protonated and lithiated 2,5-disubstituted-1,3,4-oxadiazoles. J Am Soc Mass Spectrom 14, 289–294 (2003). https://doi.org/10.1016/S1044-0305(03)00005-9
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DOI: https://doi.org/10.1016/S1044-0305(03)00005-9