Characterization of oxygenated derivatives of isoprene related to 2-methyltetrols in Amazonian aerosols using trimethylsilylation and gas chromatography/ion trap mass spectrometry

W. Wang, I. Kourtchev, B. Graham, J. Cafmeyer, W. Maenhaut, M. Claeys

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108 Citations (Scopus)

Abstract

In the present study, we have tentatively identified the structures of three oxygenated derivatives of isoprene in Amazonian rain forest aerosols as the C5 alkene triols, 2‐methyl‐1,3,4‐trihydroxy‐1‐butene (cis and trans ) and 3‐methyl‐2,3,4‐trihydroxy‐1‐butene. The formation of these oxygenated derivatives of isoprene can be explained by acid‐catalyzed ring opening of epoxydiol derivatives of isoprene, namely, 1,2‐epoxy‐2‐methyl‐3,4‐dihydroxybutane and 1,2‐dihydroxy‐2‐methyl‐3,4‐epoxybutane. The structural proposals of the C5 alkene triols were based on chemical derivatization reactions and detailed interpretation of electron and chemical ionization mass spectral data, including data obtained from first‐order mass spectra, deuterium labeling of the trimethylsilyl methyl groups, and MS2 ion trap experiments. The characterization of 2‐methyl‐1,3,4‐trihydroxy‐1‐butene (cis and trans ) and 3‐methyl‐2,3,4‐trihydroxy‐1‐butene in forest aerosols is important from an atmospheric chemistry viewpoint in that these compounds hint at the formation of intermediate isomeric epoxydiol derivatives of isoprene and as such provide mechanistic insights into the formation of the previously reported 2‐methyltetrols through photooxidation of isoprene.
Original languageEnglish
Pages (from-to)1343-1351
Number of pages9
JournalRapid Communications in Mass Spectrometry
Volume19
Issue number10
Early online date26 Apr 2005
DOIs
Publication statusPublished - 30 May 2005
Externally publishedYes

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