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. 2017 Feb 17:1485:120-130.
doi: 10.1016/j.chroma.2017.01.024. Epub 2017 Jan 10.

Retention behavior of isomeric polycyclic aromatic sulfur heterocycles in gas chromatography on stationary phases of different selectivity

Walter B Wilson  1 , Lane C Sander  2 , Jorge O Oña-Ruales  2 , Stephanie G Mössner  2 , Leonard M Sidisky  3 , Milton L Lee  4 , Stephen A Wise  2
Affiliations

Retention behavior of isomeric polycyclic aromatic sulfur heterocycles in gas chromatography on stationary phases of different selectivity

Walter B Wilson et al. J Chromatogr A. .

Abstract

Retention indices for 48 polycyclic aromatic sulfur heterocycles (PASHs) were determined using gas chromatography with three different stationary phases: a 50% phenyl phase, a 50% liquid crystalline dimethylpolysiloxane (LC-DMPS) phase, and an ionic liquid (IL) phase. Correlations between the retention behavior on the three stationary phases and PASH geometry (L/B and T, i.e., length-to-breadth ratio and thickness, respectively) were investigated for the following four isomer sets: (1) 4 three-ring molecular mass (MM) 184Da PASHs, (2) 13 four-ring MM 234Da PASHs, (3) 10 five-ring MM 258Da PASHs, and (4) 20 five-ring MM 284Da PASHs. Correlation coefficients for retention on the 50% LC-DMPS vs L/B ranged from r=0.50 (MM 284Da) to r=0.77 (MM 234Da). Correlation coefficients for retention on the IL phase vs L/B ranged from r=0.31 (MM 234Da) to r=0.54 (MM 284Da). Correlation coefficients for retention on the 50% phenyl vs L/B ranged from r=0.14 (MM 258Da) to r=0.59 (MM 284Da). Several correlation trends are discussed in detail for the retention behavior of PASH on the three stationary phases.

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Figures

Fig. 1
Fig. 1
Molecular structures and molecular shape parameters (L/B and T) of the three-ring and four-ring PASHs included in the present study.
Fig. 2
Fig. 2
Molecular structures and molecular shape parameters (L/B and T) of the five-ring PASHs with MM 258 Da and 284 Da included in the present study.
Fig. 3
Fig. 3
GC separations of the four three-ring PASH isomers with SIM for the m/z 184 ion on three different stationary phases.
Fig. 4
Fig. 4
GC separations of the 13 four-ring PASH isomers with SIM for the m/z 234 ion on three different stationary phases.
Fig. 5
Fig. 5
GC separations of the 10 peri-condensed five-ring PASH isomers with MM 258 Da with SIM for the m/z 258 ion on three different stationary phases.
Fig. 6
Fig. 6
GC separations of the 20 cata-condensed five-ring PASH isomers with MM 284 Da with SIM for the m/z 284 ion on three different stationary phases.
Fig. 7
Fig. 7
Plots of retention on the 50% phenyl versus L/B values for the (A) 4 three-ring PASHs MM 184 Da isomers, (B) 13 four-ring PASHs MM 234 Da isomers, (C) 10 peri-condensed five-ring PASHs MM 258 Da isomers, and (D) 20 cata-condensed five-ring PASHs MM 284 Da isomers.
Fig. 8
Fig. 8
Plots of retention on the 50% LC-DMPS versus L/B values for the (A) 4 three-ring PASHs MM 184 Da isomers, (B) 13 four-ring PASHs MM 234 Da isomers, (C) 10 peri-condensed five-ring PASHs MM 258 Da isomers, and (D) 20 cata-condensed five-ring PASHs MM 284 Da isomers.
Fig. 9
Fig. 9
Plots of retention on the ionic liquid phase versus L/B values for the (A) 4 three-ring PASHs MM 184 Da isomers, (B) 13 four-ring PASHs MM 234 Da isomers, (C) 10 peri-condensed five-ring PASHs MM 258 Da isomers, and (D) 20 cata-condensed five-ring PASHs MM 284 Da isomers.
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