Characterization of vinyl-substituted, carbon-carbon double bonds by GC/FT-IR analysis

Analytical Chemistry
A Svatos, A B Attygalle

Abstract

Vapor-phase infrared spectra allow the determination of the stereochemistry of carbon-carbon double bonds conjugated with a vinyl group. Cis and trans isomers of unsubstituted 1,3-alkadienes can be differentiated on the basis of the differences observed in the 900-1000 cm-1 region (spectra of cis isomers show two bands at 993 and 906 cm-1, while those of trans compounds show three absorptions at 998, 949, and 902 cm-1) and the 1590-1650 cm-1 region (the C=C stretch bands are observed at 1595 and 1642 cm-1 for cis compounds and at 1604 and 1650 cm-1 for trans compounds). Compounds bearing CH2=CHC(CH3)=CHCH2- and CH2=CHC(=CH2)-CH2- structural moieties, referred to as alpha- and beta-type compounds, are frequently encountered as natural products. For compounds bearing alpha-type groups, the cis/trans configuration of the trisubstituted double bond can be determined unambiguously. An absorption at 3095-3091 cm-1, for the =CH2 stretch vibration, is common to both of these groups; however, due to the presence of two =CH2 groups, the relative intensity of the band is much higher for beta-type compounds. For alpha-type compounds, a cis configuration at the C-3 carbon atom is characterized by a =CH2 wag absorption at 907-906 cm-1. For b...Continue Reading

Citations

Aug 1, 2007·Journal of Chemical Ecology·Rafal PiskorskiIrena Valterová
May 3, 2012·Journal of Chemical Ecology·Jana KrasulováIrena Valterová
Sep 21, 2000·Biochemical Systematics and Ecology·P VrkocováB Koutek
Oct 30, 2015·Journal of Colloid and Interface Science·Suzana HamdanIsiah M Warner
Sep 19, 2002·Journal of Agricultural and Food Chemistry·Dimitra J DafereraMoschos G Polissiou
Sep 28, 2021·Natural Product Research·Marius Balemaken MissiDieudonné Emmanuel Pegnyemb

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