A Mass Spectrometric Study of Reactions within Halogenated Benzene Rings and Ammonia
Butterworth, Kristin Marie
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Over the past two decades, much attention has been given to the study of cluster ions. One of the main areas of interest is the solvation of substituted benzenes by various solvents in the gas phase. This research focuses on the solvation of halogenated benzenes by ammonia. An intense molecular beam allows for the formation of large clusters which are then analyzed by a triple quadrupole mass spectrometer. The first and second studies focus on singly halogenated benzenes and ammonia and probe the fragmentation and reactions that occur within these charged clusters. Large differences were noted dependent on the identity of the halogen present. The third study consists of 1,3,5-trifluorobezene and trifluoromethyl benzene. In this study, fragmentation was shown to be the dominant pathway. The final study focuses on the reactions of 1,4-chlorofluorobenzene and ammonia. Within all of these systems, Lewis acid-base interactions were shown to dictate the structures formed and Sn2 reactions were seen to occur in all but 1,3,5-trifluorobenzene and trifluoromethyl benzene.