THE GAS-PHASE REACTION OF NITRONIUM ION WITH ETHYLENE - AN EXPERIMENTAL AND THEORETICAL-STUDY

The addition of NO2+ to ethylene, the prototypal electrophilic nitrati on of a pi system and the focus of considerable theoretical interest a s a model of aromatic nitration, has been studied in the gas phase by FT-ICR, MIKE, and CAD mass spectrometry, complemented by ab initio cal culations at the MP2/6-31+G level of theory. The results provide a cl earcut answer to the principal mechanistic question addressed, showing that the reaction yields a O-nitroso product, probably CH3CHONO+, rat her than a C-nitrated product.