Isoprene is a volatile organic compound (VOC) that is emitted by plants into the atmosphere in large quantities. The isoprene undergoes reactions with other products that are present in the atmosphere such as hydroxyl radicals, ozone, and nitrates to potentially produce secondary organic aerosols (SOA) that may impact both air quality and climate. The nighttime atmospheric chemistry involves nitrates as the primary reactant with the isoprene and is poorly understood. We have previously synthesized and characterized a specific isoprene hydroxyl nitrate ester from an isoprene epoxide for kinetic and mechanistic studies related to the understanding of nighttime atmospheric chemistry. Under acidic and non-acidic conditions, the epoxide should form different products due to mechanistic reasons. However, one of the epoxides generated the same hydroxy nitrate ester under two mechanistically different nitration conditions. In this presentation, we describe the synthesis, purification, and characterization of new isoprene nitrates using the wet organic chemistry protocols. The chemistry involves regioselective reactions of epoxides with nitrate nucleophiles. The overall goal of this project is to gain insight into atmospheric chemistry with an emphasis on relatively unexplored nighttime chemistry.

Synthesis, purification, characterization, and gas phase studies of atmospherically relevant and model hydroxy nitrate esters

245th National Meeting (2013)

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