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Poster Presentations
Day 2, June 23（Mon.）
Room P (Maesato East, Foyer, Ocean Wing)
- 2P-PM-32
A Mass Spectrometric Study of the Role of Water on the Paternò-Büchi (PB) Reaction between 2-Acetylpyridine and Unsaturated Fatty Acids
(CUHK)
oDanna Hu
The Paternò-Büchi (PB) reaction using 2-acetylpyridine as the charge-tagging PB reagent in combination with tandem mass spectrometry (MS/MS) has been developed as an effective method for determining positions of C=C bonds in unsaturated fatty acids. Recently, it was found that the presence of water in the reaction solution could greatly enhance the yield of the PB reaction. It was observed that increasing water content could increase the yield of PB reaction. However, this effect was complicated by the Norrish type II reactions, and the yield of PB product was found to be maximized at 30% water in water/acetonitrile binary system. At higher water content conditions, the reaction products were dominated by the isomeric products derived from the Norrish type II-A reaction, which was tentatively attributed to the increasing production of hydroxyl radicals through the photolysis of water molecules under 254 nm UV illumination. Furthermore, the exact role of water on facilitating the PB reaction was evaluated as the ‘in-water' catalysis in which aggregates of oleic acid might be formed at elevated water content. These microscopic heterogeneous surfaces might catalyze the PB reaction by bring both reaction parties together more efficiently.