Normal-Phase Liquid Chromatography Retention Behavior Of Polycyclic Aromatic Sulfur Heterocycles And Alkyl-Substituted Polycyclic Aromatic Sulfur Heterocycle Isomers On An Aminopropyl Stationary Phase

Keywords

Alkyl-substituted polycyclic aromatic sulfur heterocycles; Non-planarity; Normal-phase liquid chromatography; Polycyclic aromatic sulfur heterocycles; Retention index

Abstract

Retention indices for 67 polycyclic aromatic sulfur heterocycles (PASHs) and 80 alkyl-substituted PASHs were determined using normal-phase liquid chromatography (NPLC) on an aminopropyl (NH2) stationary phase. The retention behavior of PASH on the NH2 phase is correlated with the number of aromatic carbon atoms and two structural characteristics have a significant influence on their retention: non-planarity (thickness, T) and the position of the sulfur atom in the bay-region of the structure. Correlations between solute retention on the NH2 phase and T of PASHs were investigated for three cata-condensed (cata-) PASH isomer groups: (a) 13 four-ring molecular mass (MM) 234 Da cata-PASHs, (b) 20 five-ring MM 284 Da cata-PASHs, and (c) 12 six-ring MM 334 Da cata-PASHs. Correlation coefficients ranged from r = −0.49 (MM 234 Da) to r = −0.65 (MM 334 Da), which were significantly lower than structurally similar PAH isomer groups (r = −0.70 to r = −0.99). The NPLC retention behavior of the PASHs are compared to similar results for PAHs.

Publication Date

2-1-2018

Publication Title

Analytical and Bioanalytical Chemistry

Volume

410

Issue

5

Number of Pages

1511-1524

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1007/s00216-017-0795-7

Socpus ID

85038020998 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/85038020998

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