Mass spectrometric study of some protonated and lithiated 2,5-disubstituted-1,3,4-oxadiazoles |
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Authors: | Frański Rafał Eitner Krystian Schroeder Grzegorz Szwajka Oles P |
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Institution: | Faculty of Chemistry, Adam Mickiewicz University, Poznań, Poland. franski@main.amu.edu.pl |
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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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