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Journal Article

Gas-phase infrared spectroscopy for determination of double-bond configuration of some polyunsaturated pheromones and related compounds

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Attygalle, A. B., Svatoš, A., Wilcox, C., & Voennan, S. (1995). Gas-phase infrared spectroscopy for determination of double-bond configuration of some polyunsaturated pheromones and related compounds. Analytical Chemistry, 67(9), 1558-1567. doi:10.1021/ac00105a014.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0015-0E37-0
Gas-phase Fourier transform infrared spectroscopy allows the determination of the geometric configuration of disubstituted carbon-carbon double bonds present in linear polyunsaturated compounds on the basis of the characteristic absorptions observed in the 3036-3011 and 982-947 cm(-1) regions. Although the 3036-3011 cm(-1) band, attributable to a =CH stretch vibration, is conventionally considered to be unreliable for cis/trans determinations, data obtained from a large number of mono- and polyunsaturated acetates show that many useful deductions can be based on this absorption, Double bonds of the RCH=CHR' type separated by at least two methylene groups, present in polyunsaturated compounds, give rise to an absorption at 3013-3011 cm(-1) if the double bonds are not proximal to a functional group or a terminal methyl group, Cis dienes whose double bonds are separated by only a single methylene group show the cis =CH stretch band at 3017 cm(-1). For methylene-interrupted polyenes, this band shows a gradual hypsochromic shift as the unsaturation increases, Furthermore, a band at 1391 cm(-1) was recognized to represent the deformation vibration of the CH2 groups located between the double bonds, The intensity of this band is proportional to the number of skipped methylene groups. I None of the isolated or methylene-interrupted dienes bearing only trans double bonds showed any significant absorptions above 3000 cm(-1). However, spectra of trans-trans conjugated compounds show a =CH stretch band at 3016-3012 cm(-1) as a well-defined shoulder on the high-frequency side of the CH2 asymmetric stretch band, in addition to the wag absorption observed at 984-982 cm(-1), which is highly characteristic for trans-trans conjugated compounds, The spectra of cis-trans or trans-cis conjugated compounds are virtually identical and show a characteristic ''fingerprint'' consisting of two bands of similar intensity at 978-976 and 949-946 cm(-1), in addition to the =C-H stretch band observed at 3021-3017 cm(-1), interestingly, not only are the spectra of conjugated cis-cis compounds devoid of any significant absorption in the 982-947 cm(-1) region, but also the =CH stretch band is broad and appears as a poorly defined shoulder on the high-frequency edge of the CH2 asymmetric stretch band.