Abstract
In an attempt to produce the 2-norbornyl cation (2NB+) in the gas phase, protonation of norbornene was accomplished in a pulsed discharge ion source coupled with a supersonic molecular beam. The C7H11+ cation was size-selected in a time-of-flight mass spectrometer and investigated with infrared laser photodissociation spectroscopy using the method of “tagging” with argon. The resulting vibrational spectrum, containing sharp bands in the CH stretching and fingerprint regions, was compared to that predicted by computational chemistry. However, the measured spectrum did not match that of 2NB+, prompting a detailed computational study of other possible isomers of C7H11+. This study finds five isomers more stable than 2NB+. The spectrum obtained corresponds to the 1,3-dimethylcyclopentenyl cation, the global minimum-energy structure for C7H11+, which is produced through an unanticipated ring-opening rearrangement path.
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