Mass Spectroscopy and Chromatography of the Trichloromethyl Radical Adduct of Phenyl Ter T-Butyl Nitrone

Abstract

Positive structural identification of the PBN-trichloromethyl spin adduct in vim was accomplished with the use of high pressure liquid chromatography and/or gas chromatography coupled with mass spectrome-try. Both thin layer and liquid chromatography were used to separate a complex mixture of compounds from rat liver extracts treated with CCI, in vitro and in vivo. Deuterated PBN's (PBN-d, text-butyl deuteration, or PBN-d₁₄; both phenyl and tert-butyl deuteration) were also used to aid in the mass spectral analysis of spin adducts from liver extracts of CCI, exposed rat livers, since the rerr-butyl group fragment ion, C₄D₉+ (m/z = 66) is always present for PBN and PBN spin adducts. In addition, the masses of the ion peaks increase by the amount of deuteration, i.e. an increase of 9 for PBN-d, or PBN-d₁₄ in comparison to normally synthesized PBN.

Key Words:

• α-Phenyl tert-butyl nitrone (PBN)
• carbon tetrachloride (CCI)
• PBN-trichloromethyl adduct (PBN-CCI)
• thin layer chromarography (TLC)
• high pressure chromatography (HPLC)
• gas chromatography/mass spectrometry (GC/MS)
• electron spin resonance (ESR)