Correlation of vapor phase infrared spectra and regioisomeric structure in synthetic cannabinoids

Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
Lewis W SmithC Randall Clark

Abstract

The twelve 1-n-pentyl-2-, 3-, 4-, 5-, 6- and 7-(1- and 2-naphthoyl)-indoles each have the same substituents attached to the indole ring, identical elemental composition (C24H23NO) yielding identical nominal and accurate masses. These twelve isomers cover all possible positions of carbonyl bridge substitution for both indole (positons 2-7) and naphthalene rings (positions 1 and 2). Regioisomeric compounds can represent significant challenges for mass based analytical methods however, infrared spectroscopy is a powerful tool for the identification of positional isomers in organic compounds. The vapor phase infrared spectra of these twelve uniquely similar compounds were evaluated in GC-IR experiments. These spectra show the bridge position on the indole ring is a dominating influence over the carbonyl absorption frequency observed for these compounds. Substitution on the pyrrole moiety of the indole ring yields the lowest CO frequency values for position 2 and 3 giving a narrow range from 1656 to 1654cm-1. Carbonyl absorption frequencies are higher when the naphthoyl group is attached to the benzene portion of the indole ring yielding absorption values from 1674 to 1671cm-1. The aliphatic stretching bands in the 2900cm-1 region y...Continue Reading

Citations

Jan 2, 2021·Forensic Science International : Synergy·Nicole S Jones, Jeffrey H Comparin
Oct 26, 2020·Forensic Science International : Synergy·Hui Zhi Shirley LeeTiong Whei Angeline Yap

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