Normal-phase liquid chromatography retention behavior of polycyclic aromatic sulfur heterocycles (PASHs) and alkyl-substituted PASH isomers on an aminopropyl stationary phase

Published

December 14, 2017

Author(s)

Walter Wilson, Hugh Hayes, Lane Sander, Andres Campiglia, Stephen Wise

Abstract

Retention indices for 67 polycyclic aromatic sulfur heterocycles (PASHs) and 80 alkyl- substituted PASHs were determined using normal-phase liquid chromatography (NPLC) on a aminopropyl (NH2) stationary phase. The retention behavior of PASH on the NH2 phase is correlated to the total number of aromatic carbon atoms and two structural characteristics were found to 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 the retention behavior on the NH2 phase and T of PASHs were investigated for three cata-condensed (cata-) PASH isomer groups: (1) 13 four-ring MM 234 Da cata-PASHs, (2) 20 five-ring MM 284 Da cata-PASHs, and (3) 12 six-ring MM 334 Da cata-PASHs. Correlation coefficients ranged from r = -0.17 (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).

Citation

Journal of Chromatography A

Pub Type

Journals

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DOI Link

Keywords

normal-phase liquid chromatography, polycyclic aromatic sulfur heterocycles, aminopropyl stationary phase, retention indices

Citation

Wilson, W. , Hayes, H. , Sander, L. , Campiglia, A. and Wise, S. (2017), Normal-phase liquid chromatography retention behavior of polycyclic aromatic sulfur heterocycles (PASHs) and alkyl-substituted PASH isomers on an aminopropyl stationary phase, Journal of Chromatography A, [online], https://doi.org/10.1007/s00216-017-0795-7 (Accessed March 13, 2025)