The chemistry of perfluoroisobutylene (PFIB) with nitrone and nitroso spin traps: an EPR/Spin trapping study

While applying electron paramagnetic resonance (EPR)/Spin Trapping techniques, several reactive intermediate species were identified in the reaction of perfluoroisobutylene (PFIB) with nitrone and nitroso spin trap agents: the carbon dioxide radical anion (CO2.-), a carbonyl fluoride intermediate (COF), and vinyl carbanions of PFIB. The reaction of PFIB with N-t-butyl-alpha-phenylnitrone (PBN) forms a dipolar ion which undergoes electron transfer reactions generating stable nitrone spin adducts. Nitroso compounds reacted with carbanions derived from PFIB, which raises the possibility that electron transfer reactions of this type might account for the observed nitroxides. Our results suggest that PFIB undergoes some type of electron transfer reaction leading to several reactive intermediate species (RIS). The implications of these observations on pulmonary damage caused by inhalation of PFIB are discussed.